Pyrazine compound

ABSTRACT

Provided is a compound represented by formula (I): 
                         
or an N-oxide compound thereof, wherein the variable groups are as defined in the specification. Also provided is an arthropod pest control agent containing a compound represented by formula (I) and an inert carrier. The compound represented by formula (I) and arthropod pest control agent exhibit an excellent controlling effect against arthropod pests.

CROSS-REFERENCE TO RELATED APPLICATION

This application is a Division of U.S. patent application Ser. No.15/766,034 filed Apr. 5, 2018, now allowed, which is a Section 371 ofInternational Application No. PCT/JP2016/080410, filed Oct. 13, 2016,which was published in the Japanese language on Apr. 20, 2017, underInternational Publication No. WO 2017/065228 A1, which claims priorityunder 35 U.S.C. § 119(b) to Japanese Application No. 2015-204376, filedOct. 16, 2015, Japanese Application No. 2015-208639, filed Oct. 23, 2015and Japanese Application No. 2016-149448, filed Jul. 29, 2016, thedisclosures of all of which are incorporated herein by reference intheir entireties.

TECHNICAL FIELD

The present invention is related to a certain class of pyrazine compoundand its use for controlling harmful arthropods.

BACKGROUND ART

To date, some compounds for controlling harmful arthropods have beendeveloped and come into practical use. Also, a certain class ofcompounds has been known to be effective for controlling harmfulorganisms (see Patent Document 1).

CITATION LIST Patent Document

Patent Document 1: JP2000-26421 A

SUMMARY OF THE INVENTION Problems to be Solved by Invention

An object of the present invention is to provide a compound having anexcellent efficacy for controlling harmful arthropods.

Means to Solve Problems

The present invention provides, for example, the following embodiments.

[1] A compound represented by formula (I) or its N oxide compound:

[wherein

A¹ represents a nitrogen atom or a CR⁴;

R⁴ represents a hydrogen atom, a OR²⁷, a NR²⁷R²⁸, a cyano group, a nitrogroup, or a halogen atom;

R¹ represents a C2-C10 chain hydrocarbon group having one or morehalogen atoms, a (C1-C5 alkoxy)C2-C5 alkyl group having one or morehalogen atoms, a (C1-C5 alkylsulfanyl)C2-C5 alkyl group having one ormore halogen atoms, a (C1-C5 alkylsulfinyl)C2-C5 alkyl group having oneor more halogen atoms, a (C1-C5 alkylsulfonyl)C2-C5 alkyl group havingone or more halogen atoms, a (C3-C7 cycloalkyl)C1-C3 alkyl group havingone or more substituents selected from Group G, or a C3-C7 cycloalkylgroup having one or more substituents selected from Group G;

R² represents a C1-C6 alkyl group optionally having one or more halogenatoms, a cyclopropylmethyl group, or a cyclopropyl group;

q represents 0, 1, 2, or 3;

R³ represents independently of each other, a C1-C6 chain hydrocarbongroup optionally having one or more substituents selected from Group B,a phenyl group optionally having one or more substituents selected fromGroup D, a 5 or 6 membered aromatic heterocyclic group optionally havingone or more substituents selected from Group D, a OR¹², a NR¹¹R¹², aNR^(11a)R^(12a), a NR²⁹NR¹¹R¹², a NR²⁹OR¹¹, a NR¹¹C(O)R¹³, aNR²⁹NR¹¹C(O)R¹³, a NR¹¹C(O)OR¹⁴, a NR²⁹NR¹¹C(O)OR¹⁴, a NR¹¹C(O)NR¹⁵R¹⁶,a NR²⁴NR¹¹C(O)NR¹⁵R¹⁶, a N═CHNR¹⁵R¹⁶, a N═S(O)_(x)R¹⁵R¹⁶, a S(O)_(y)R¹⁵,a C(O)OR¹⁷, a C(O)NR¹¹R¹², a cyano group, a nitro group, or a halogenatom, and when q is 2 or 3, a plurality of R³ may be identical ordifferent;

p represents 0, 1, or 2,

R⁶ represents independently of each other, a C1-C6 alkyl groupoptionally having one or more halogen atoms, a OR¹⁸, a NR¹⁸R¹⁹, a cyanogroup, a nitro group, or a halogen atom, and when p is 2, a plurality ofR⁶ may be identical or different;

R¹⁷, R¹⁸, R¹⁹, R²⁴ and R²⁹ represent independently of each other ahydrogen atom, or a C1-C6 chain hydrocarbon group optionally having oneor more halogen atoms;

R¹² represents a hydrogen atom, a C1-C6 chain hydrocarbon groupoptionally having one or more halogen atoms, a C1-C6 alkyl group havingone substituent selected from Group F, or a S(O)₂R²³;

R²³ represents a C1-C6 chain hydrocarbon group optionally having one ormore halogen atoms, or a phenyl group optionally having one or moresubstituents selected from Group D;

R^(11a) and R^(12a) combine together with a nitrogen atom to which theyare attached to form a 3 to 7 membered nonaromatic heterocyclic groupoptionally having one or more substituents selected from Group E {the 3to 7 membered nonaromatic heterocyclic group represents aziridine,azetidine, pyrrolidine, imidazoline, imidazolidine, piperidine,tetrahydropyrimidine, hexahydropyrimidine, piperazine, azepane,oxazolidine, isooxazolidine, 1,3-oxazinane, morpholine, 1,4-oxazepane,thiazolidine, isothiazolidine, 1,3-thiazinane, thiomorpholine, or1,4-thiazepane};

R¹³ represents a hydrogen atom, a C1-C6 chain hydrocarbon groupoptionally having one or more halogen atoms, a C3-C7 cycloalkyl groupoptionally having one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3alkyl group optionally having one or more halogen atoms, a phenyl groupoptionally having one or more substituents selected from Group D, or a 5or 6 membered aromatic heterocyclic group optionally having one or moresubstituents selected from Group D;

R¹⁴ represents a C1-C6 chain hydrocarbon group optionally having one ormore halogen atoms, a C3-C7 cycloalkyl group optionally having one ormore halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group optionallyhaving one or more halogen atoms, or a phenylC1-C3 alkyl group {thephenyl moiety in the phenylC1-C3 alkyl group may optionally have one ormore substituents selected from Group D};

R¹⁵ and R¹⁶ represent independently of each other, a C1-C6 alkyl groupoptionally having one or more halogen atoms;

R²⁷ and R²⁸ represent independently of each other, a hydrogen atom, or aC1-C6 alkyl group optionally having one or more halogen atoms;

n and y represent independently of each other, 0, 1, or 2;

x represents 0 or 1;

Group B: a group consisting of a C1-C6 alkoxy group optionally havingone or more halogen atoms, a C3-C6 alkenyloxy group optionally havingone or more halogen atoms, a C3-C6 alkynyloxy group optionally havingone or more halogen atoms, a C1-C6 alkylsulfanyl group optionally havingone or more halogen atoms, a C1-C6 alkylsulfinyl group optionally havingone or more halogen atoms, a C1-C6 alkylsulfonyl group optionally havingone or more halogen atoms, a C3-C6 cycloalkyl group optionally havingone or more halogen atoms, a cyano group, a hydroxy group, and a halogenatom;

Group C: a group consisting of a C1-C6 chain hydrocarbon groupoptionally having one or more halogen atoms, a C1-C6 alkoxy groupoptionally having one or more halogen atoms, a C3-C6 alkenyloxy groupoptionally having one or more halogen atoms, a C3-C6 alkynyloxy groupoptionally having one or more halogen atoms, and a halogen atom;

Group D: a group consisting of a C1-C6 chain hydrocarbon groupoptionally having one or more halogen atoms, a hydroxy group, a C1-C6alkoxy group optionally having one or more halogen atoms, a C3-C6alkenyloxy group optionally having one or more halogen atoms, a C3-C6alkynyloxy group optionally having one or more halogen atoms, a sulfanylgroup, a C1-C6 alkylsulfanyl group optionally having one or more halogenatoms, a C1-C6 alkylsulfinyl group optionally having one or more halogenatoms, a C1-C6 alkylsulfonyl group optionally having one or more halogenatoms, an amino group, a NHR²¹, a NR²¹R²², a C(O)R²¹, a OC(O)R²¹, aC(O)OR²¹, a cyano group, a nitro group, and a halogen atom {R²¹ and R²²represent independently of each other a C1-C6 alkyl group optionallyhaving one or more halogen atoms};

Group E: a group consisting of a C1-C6 chain hydrocarbon groupoptionally having one or more halogen atoms, a C1-C6 alkoxy groupoptionally having one or more halogen atoms, a C3-C6 alkenyloxy groupoptionally having one or more halogen atoms, a C3-C6 alkynyloxy groupoptionally having one or more halogen atoms, a halogen atom, an oxogroup, a hydroxy group, a cyano group, and a nitro group;

Group F: a group consisting of a C1-C6 alkoxy group optionally havingone or more halogen atoms, an amino group, a NHR²¹, a NR²¹R²², a cyanogroup, a phenyl group optionally having one or more substituentsselected from Group D, a 5 or 6 membered aromatic heterocyclic groupoptionally having one or more substituents selected from Group D, aC3-C7 cycloalkyl group optionally having one or more halogen atoms, anda 3 to 7 membered nonaromatic heterocyclic group optionally having oneor more substituents selected from Group C;

Group G: a group consisting of a halogen atom, and a C1-C6 haloalkylgroup].

[2] The compound described in [1] wherein R⁴ represents a hydrogen atomor a halogen atom, and R³ represents a C1-C6 chain hydrocarbon groupoptionally having one or more halogen atoms, a phenyl group optionallyhaving one or more substituents selected from Group D, a 6 memberedaromatic heterocyclic group containing one to two nitrogen atoms {the 6membered aromatic heterocyclic group optionally has one or moresubstituents selected from Group D}, a 5 membered aromatic heterocyclicgroup containing one to four nitrogen atoms {the 5 membered aromaticheterocyclic group optionally has one or more substituents selected fromGroup D}, a OR¹², a NR¹¹R¹², or a halogen atom.[3] The compound described in [1] wherein R³ represents a C1-C6 alkylgroup having one or more halogen atoms, a OR¹², a NR¹¹R¹², or a halogenatom, and R¹¹ and R¹² represent independently of each other a hydrogenatom or a C1-C3 alkyl group optionally having one or more halogen atoms.[4] The compound described in [1] wherein q is 0.[5] The compound described in any one of [1] to [4] wherein p is 0 or 1,and R⁶ represents a C1-C6 alkyl group optionally having one or morehalogen atoms, or a halogen atom.[6] The compound described in any one of [1] to [4] wherein p is 0.[7] The compound described in any one of [1] to [5] wherein R¹represents a C2-C10 haloalkyl group.[8] The compound described in any one of [1] to [6] wherein R¹represents a C2-C10 fluoroalkyl group.[9] The compound described in any one of [1] to [6] wherein R¹represents a C2-C10 alkyl group having two or more fluorine atoms.[10] The compound described in any one of [1] to [6] wherein R¹represents a C3-C5 alkyl group having four or more fluorine atoms.[11] The compound described in any one of [1] to [10] wherein R²represents a C1-C6 alkyl group optionally having one or more halogenatoms.[12] The compound described in any one of [1] to [10] wherein R²represents an ethyl group.[13] The compound described in [1] wherein

R¹ represents a C2-C10 haloalkyl group;

R² represents an ethyl group;

q is 0 or 1, and R³ represents a C1-C6 alkyl group optionally having oneor more halogen atoms, or a halogen atom; and

p is 0 or 1, and R⁶ represents a C1-C6 alkyl group optionally having oneor more halogen atoms, or a halogen atom.

[14] The compound described in [1] wherein

R¹ represents a C3-C5 alkyl group having four or more fluorine atoms;

R² represents an ethyl group;

q is 0; and

p is 0.

[15] A composition comprising the compound described in any one of [1]to [14], and one or more ingredients selected from the group consistingof Groups (a), (b), (c), and (d):

Group (a): a group consisting of insecticidal ingredients, miticidalingredients, and nematicidal ingredients;

Group (b): fungicidal ingredients;

Group (c): plant growth modulating ingredients; and

Group (d): phytotoxicity-reducing ingredients.

[16] A method for controlling a harmful arthropod which comprisesapplying an effective amount of the compound described in any one of [1]to [14] or the composition described in [15] to a harmful arthropod or ahabitat where a harmful arthropod lives.

[17] A method for controlling a harmful arthropod which comprisesapplying an effective amount of the compound described in any one of [1]to [14] or the composition described in [15] to a plant or soil forgrowing a plant.

[18] A method for controlling a harmful arthropod which comprisesapplying an effective amount of the compound described in [1] to [14] orthe composition described in [15] to a seed or bulb.

[19] A seed or bulb carrying an effective amount of the compounddescribed in any one of [1] to [14] or the composition described in[15].

[20] An agent for controlling a harmful arthropod comprising thecompound described in any one of [1] to [14] or the compositiondescribed in [15], and an inert carrier.

[21] A compound represented by formula (M-3):

[wherein

A¹ represents a nitrogen atom or a CR⁴;

R⁴ represents a hydrogen atom, a OR²⁷, a NR²⁷R²⁸, a cyano group, a nitrogroup, or a halogen atom;

R² represents a C1-C6 alkyl group optionally having one or more halogenatoms, a cyclopropylmethyl group, or a cyclopropyl group;

q represents 0, 1, 2, or 3;

R³ represents independently of each other a C1-C6 chain hydrocarbongroup optionally having one or more substituents selected from Group B,a phenyl group optionally having one or more substituents selected fromGroup D, a 5 or 6 membered aromatic heterocyclic group optionally havingone or more substituents selected from Group D, a OR¹², a NR¹¹R¹², aNR^(11a)R^(12a), a NR²⁹NR¹¹R¹², a NR²⁹OR¹¹, a NR¹¹C(O) R¹³, a NR²⁹NR¹¹c(0) a NR¹¹C(O)OR¹⁴, a NR²⁹NR¹¹C(O) OR¹⁴, a NR¹¹C(O) NR¹⁵R¹⁶, aNR²⁴NR¹¹C(O) NR¹⁵R¹⁶, a N═CHNR¹⁵R¹⁶, a N═S(O)_(x)R¹⁵R¹⁶, a S(O)_(y)R¹⁵,a C(O)OR¹⁷, a C(O)NR¹¹R¹², a cyano group, a nitro group, or a halogenatom, and when q is 2 or 3, a plurality of R³ may be identical ordifferent;

p represents 0, 1, or 2; and

R⁶ represents independently of each other a C1-C6 alkyl group optionallyhaving one or more halogen atoms, a OR¹⁸, a NR¹⁸R¹⁹, a cyano group, anitro group, or a halogen atom, and when p is 2, a plurality of R⁶ maybe identical or different].

[22] A compound represented by formula (M-4):

[wherein

V represents a halogen atom;

A¹ represents a nitrogen atom or a CR⁴;

R⁴ represents a hydrogen atom, a OR²⁷, a NR²⁷R²⁸, a cyano group, a nitrogroup, or a halogen atom;

R² represents a C1-C6 alkyl group optionally having one or more halogenatoms, a cyclopropylmethyl group, or a cyclopropyl group;

q represents 0, 1, 2, or 3;

R³ represents independently of each other a C1-C6 chain hydrocarbongroup optionally having one or more substituents selected from Group B,a phenyl group optionally having one or more substituents selected fromGroup D, a 5 or 6 membered aromatic heterocyclic group optionally havingone or more substituents selected from Group D, a OR¹², a NR¹¹R¹², aNR^(11a)R^(12a), a NR²⁹NR¹¹R¹², a NR²⁹OR¹¹, a NR¹¹C(O)R¹³, aNR²⁹NR¹¹C(O)R¹³, a NR¹¹C(O)OR¹⁴, a NR²⁹NR¹¹C(O)OR¹⁴, a NR¹¹C(O)NR¹⁵R¹⁶,a NR²⁴NR¹¹C(O)NR¹⁵R¹⁶, a N═CHNR¹⁵R¹⁶, a N═S(O)_(x)R¹⁵R¹⁶, a S(O)_(y)R¹⁵,a C(O)OR¹⁷, a C(O)NR¹¹R¹², a cyano group, a nitro group, or a halogenatom, and when q is 2 or 3, a plurality of R³ may be identical ordifferent;

p represents 0, 1, or 2; and

R⁶ represents independently of each other a C1-C6 alkyl group optionallyhaving one or more halogen atoms, a OR¹⁸, a NR¹⁸R¹⁹, a cyano group, anitro group, or a halogen atom, and when p is 2, a plurality of R⁶ maybe identical or different].

[23] A compound represented by formula (M-30):

[wherein

R⁴⁰ represents a halogen atom, a C1-C4 alkoxy group, or a OR¹;

R¹ represents a C2-C10 chain hydrocarbon group having one or morehalogen atoms, a (C1-C5 alkoxy)C2-C5 alkyl group having one or morehalogen atoms, a (C1-C5 alkylsulfanyl)C2-C5 alkyl group having one ormore halogen atoms, a (C1-C5 alkylsulfinyl)C2-C5 alkyl group having oneor more halogen atoms, a (C1-C5 alkylsulfonyl)C2-C5 alkyl group havingone or more halogen atoms, a (C3-C7 cycloalkyl)C1-C3 alkyl group havingone or more substituents selected from Group G, or a C3-C7 cycloalkylgroup having one or more substituents selected from Group G;

R² represents a C1-C6 alkyl group optionally having one or more halogenatoms, a cyclopropylmethyl group, or a cyclopropyl group;

p represents 0, 1, or 2; and

R⁶ represents independently of each other a C1-C6 alkyl group optionallyhaving one or more halogen atoms, a OR¹⁸, a NR¹⁸R¹⁹, a cyano group, anitro group, or a halogen atom, and when p is 2, a plurality of R⁶ maybe identical or different].

[24] A compound represented by formula (M-31):

[wherein

R⁴⁰ represents a halogen atom, a C1-C4 alkoxy group, or a OR¹;

R¹ represents a C2-C10 chain hydrocarbon group having one or morehalogen atoms, a (C1-C5 alkoxy)C2-C5 alkyl group having one or morehalogen atoms, a (C1-C5 alkylsulfanyl)C2-C5 alkyl group having one ormore halogen atoms, a (C1-C5 alkylsulfinyl)C2-C5 alkyl group having oneor more halogen atoms, a (C1-C5 alkylsulfonyl)C2-C5 alkyl group havingone or more halogen atoms, a (C3-C7 cycloalkyl)C1-C3 alkyl group havingone or more substituents selected from Group G, or a C3-C7 cycloalkylgroup having one or more substituents selected from Group G;

R² represents a C1-C6 alkyl group optionally having one or more halogenatoms, a cyclopropylmethyl group, or a cyclopropyl group;

p represents 0, 1, or 2; and

R⁶ represents independently of each other a C1-C6 alkyl group optionallyhaving one or more halogen atoms, a OR¹⁸, a NR¹⁸R¹⁹, a cyano group, anitro group, or a halogen atom, and when p is 2, a plurality of R⁶ maybe identical or different].

Effect of Invention

The Present compound has an excellent control efficacy against harmfularthropods, and is thus useful as an active ingredient of an agent forcontrolling harmful arthropods. Also, a composition comprising thePresent compound and one or more ingredients selected from the groupconsisting of Groups (a), (b), (c) and (d) (hereinafter, referred to as“Present composition”) shows an excellent control effect against harmfularthropods.

MODE FOR CARRYING OUT THE INVENTION

The substituent(s) as described herein is/are explained.

The term of “optionally having one or more halogen atoms” representsthat when two or more halogen atoms are present, these halogen atoms maybe identical to or different from each other.

The expression of “CX-CY” as used herein represents that the number ofcarbon atom is from X to Y. For example, the expression of “C1-C6”represents that the number of carbon atom is from 1 to 6.

The term of “halogen atom” represents fluorine atom, chlorine atom,bromine atom, or iodine atom.

The term of “chain hydrocarbon group” represents an alkyl group, analkenyl group, or an alkynyl group.

Examples of the term of “alkyl group” include methyl group, ethyl group,propyl group, isopropyl group, 1,1-dimethylpropyl group,1,2-dimethylpropyl group, 1-ethylpropyl group, butyl group, tert-butylgroup, pentyl group, hexyl group, heptyl group, octyl group, nonylgroup, and decyl group.

Examples of the term of “alkenyl group” include vinyl group, 1-propenylgroup, 2-propenyl group, 1-methyl-1-propenyl group, 1-methyl-2-propenylgroup, 1,2-dimethyl-1-propenyl group, 1,1-dimethyl-2-propenyl group,1-ethyl-1-propenyl group, 1-ethyl-2-propenyl group, 3-butenyl group,4-pentenyl group, 5-hexenyl group, heptenyl group, octenyl group,nonenyl group, and decenyl group.

Examples of the term of “alkynyl group” includes ethynyl group,1-propynyl group, 2-propynyl group, 1-methyl-2-propynyl group,1,1-dimethyl-2-propynyl group, 1-ethyl-2-propynyl group, 2-butynylgroup, 4-pentynyl group, 5-hexynyl group, heptynyl group, octinyl group,nonynyl group, and decynyl group.

The term of “C2-C10 chain hydrocarbon group having one or more halogens”represents a C2-C10 alkyl group, a C2-C10 alkenyl group, a C2-C10alkynyl group, each having one or more halogens.

The term of “C2-C10 haloalkyl group” represents a group wherein one ormore hydrogen atoms in the C2-C10 alkyl group is/are substituted byhalogen atoms, and includes, for example, a C2-C10 fluoroalkyl group.Examples of the term of “C2-C10 haloalkyl group” include chloroethylgroup, 2,2,2-trifluoroethyl group, 2-bromo-1,1,2,2-tetrafluoroethylgroup, 2,2,3,3-tetrafluoropropyl group,1-methyl-2,2,3,3-tetrafluoropropyl group, perfluorohexyl group, andperfluorodecyl group.

Examples of the term of “C2-C10 fluoroalkyl group” include2,2,2-trifluoroethyl group, 2,2,3,3-tetrafluoropropyl group,1-methyl-2,2,3,3-tetrafluoropropyl group, perfluorohexyl group, andperfluorodecyl group.

Examples of the term of “C2-C10 alkyl group having two or more fluoroatoms” include 2,2,2-trifluoroethyl group, 2,2,3,3-tetrafluoropropylgroup, 1-methyl-2,2,3,3-tetrafluoropropyl group, perfluorohexyl group,and perfluorodecyl group.

Examples of the term of “C2-C10 alkyl group having four or more fluoroatoms” include 2,2,3,3-tetrafluoropropyl group,1-methyl-2,2,3,3-tetrafluoropropyl group, perfluorohexyl group, andperfluorodecyl group.

The term of “C2-C10 haloalkenyl group” represents a group wherein one ormore hydrogen atoms in the C2-C10 alkenyl group is/are substituted byhalogen atoms, and includes, for example, a C2-C10 fluoroalkenyl group.Examples of the “C2-C10 fluoroalkenyl group” includes, for example,4,4,4-trifluoro-2-butenyl group, and 2,4,4,4-tetrafluoro-2-butenylgroup.

The term of “C2-C10 haloalkynyl group” represents a group wherein one ormore hydrogen atoms in the C2-C10 alkynyl group is/are substituted byhalogen atoms, and includes, for example, a C2-C10 fluoroalkynyl group.Examples of the “C2-C10 fluoroalkynyl group” includes, for example,4,4,4-trifluoro-2-butynyl group.

Examples of the term of “C1-C6 alkyl group optionally having one or morehalogen atoms” include 2,2,2-trifluoroethyl group,2,2,3,3-tetrafluoropropyl group, and 2,2,3,4,4,4-hexafluoropropyl group.

The term of “C1-C6 chain hydrocarbon group having one or more halogenatoms” represents a C1-C6 alkyl group, a C1-C6 alkenyl group, or a C1-C6alkynyl group, each having one or more halogen atoms. The term of “C1-C6alkyl group having one or more halogen atoms” is encompassed into theabove-mentioned terms of “C1-C6 alkyl group optionally having one ormore halogen atoms” and the above-mentioned term of “C2-C10 chainhydrocarbon group having one or more halogen atoms”. The term of “C1-C6alkenyl group having one or more halogen atoms” and the term of “C1-C6alkynyl group having one or more halogen atoms” are encompassed into theabove-mentioned term of “C2-C10 chain hydrocarbon group having one ormore halogen atoms”.

Examples of the term of “cycloalkyl group” include cyclopropyl group,cyclobutyl group, cyclopentyl group, cyclohexyl group, and cycloheptylgroup.

The term of “alkoxy group” represents a monovalent group wherein theabove-mentioned “alkyl group” binds to an oxygen atom, and examples of aC1-C6 alkoxy group include methoxy, ethoxy, n-propoxy, i-propoxy,n-butoxy, t-butoxy, s-butoxy, and 3-methylbutoxy.

Examples of the term of “3 to 7 membered nonaromatic heterocyclic group”include aziridine, azetidine, pyrrolidine, imidazoline, imidazolidine,piperidine, tetrahydropyrimidine, hexahydropyrimidine, piperazine,azepane, oxazolidine, isooxazolidine, 1,3-oxazinane, morpholine,1,4-oxazepane, thiazolidine, isothiazolidine, 1,3-thiazinane,thiomorpholine, and 1,4-thiazepane. Examples of the 3 to 7 memberednonaromatic heterocyclic group optionally having one or moresubstituents selected from Group E include the followings:

Examples of the term of “phenylC1-C3 alkyl group {the phenyl moiety inthe phenylC1-C3 alkyl group may optionally have one or more substituentsselected from Group D}] include benzyl group, 2-fluorobenzyl group,4-chlorobenzyl group, 4-(trifluoromethyl)benzyl group, and2-[4-(trifluoromethyl)phenyl]ethyl group.

The term of “(C1-C5 alkoxy)C2-C5 alkyl group having one or more halogenatoms” represents a group wherein the (C1-C5 alkoxy) and/or the (C2-C5alkyl) have/has one or more halogen atoms, and includes, for example,2-(trifluoromethoxy) ethyl group, 2,2-difluoro-3-methoxypropyl group,2,2-difluoro-3-(2,2,2-trifluoroethoxy)propyl group, and3-(2-chloroethoxy)propyl group.

The term of “(C1-C5 alkylsulfanyl)C2-C5 alkyl group having one or morehalogen atoms” represents a group wherein the (C1-C5 alkylsulfanyl)and/or the (C2-C5 alkyl) have/has one or more halogen atoms, andincludes, for example, 2,2-difluoro-2-(trifluoromethylthio))ethyl group.

The term of “(C1-C5 alkylsulfinyl)C2-C5 alkyl group having one or morehalogen atoms” represents a group wherein the (C1-C5 alkylsulfinyl)and/or the (C2-C5 alkyl) have/has one or more halogen atoms, andincludes, for example, 2,2-difluoro-2-(trifluoromethansulfinyl)ethylgroup.

The term of “(C1-C5 alkylsulfonyl) C2-C5 alkyl group having one or morehalogen atoms” represents a group wherein the (C1-C5 alkylsulfonyl)and/or the (C2-C5 alkyl) group have/has one or more halogen atoms, andincludes, for example, 2,2-difluoro-2-(trifluoromethansulfonyl)ethylgroup.

The term of “(C3-C6 cycloalkyl)C1-C3 alkyl group having one or morehalogen atoms” represents a group wherein the (C3-C6 cycloalkyl) and/orthe (C1-C3 alkyl) has/have one or more halogen atoms, and includes, forexample, (2,2-difluorocyclopropyl)methyl group,2-cyclopropyl-1,1,2,2-tetrafluoroethyl group, and2-(2,2-difluorocyclopropyl)-1,1,2,2-tetrafluoroethyl group.

The term of “(C3-C7 cycloalkyl)C1-C3 alkyl group having one or moresubstituents selected from Group G” represents a group wherein the(C3-C7 cycloalkyl) and/or the (C1-C3 alkyl) has/have one or moresubstituents selected from Group G, and includes, for example,(2,2-difluorocyclopropyl)methyl group,[1-(trifluoromethyl)cyclopropyl]methyl group,[2-(trifluoromethyl)cyclopropyl]methyl group,2-cyclopropyl-1,1,2,2-tetrafluoroethyl group,2-cyclopropyl-3,3,3-trifluoropropyl group, and1,1,2,2-tetrafluoro-2-[2-(trifluoromethyl)cyclopropyl]ethyl group.

The term of “C3-C7 cycloalkyl group having one or more substituentsselected from Group G” includes, for example, 2,2-difluorocyclopropylgroup, 1-(2,2,2-trifluoroethyl)cyclopropyl group, and4-trifluoromethyl)cyclohexyl group,

The term of “5 or 6 membered aromatic heterocyclic group” represents a 5membered aromatic heterocyclic group or a 6 membered aromaticheterocyclic group. Examples of the 5 membered aromatic heterocyclicgroup include pyrrolyl group, furyl group, thienyl group, pyrazolylgroup, imidazolyl group, triazolyl group, tetrazolyl group, oxazolylgroup, isoxazolyl group, triazolyl group, oxadiazolyl group, andthiadiazolyl group. Examples of the membered aromatic heterocyclic groupinclude pyridyl group, pyridazinyl group, pyrimidinyl group andpyrazinyl group.

The term of “6 membered aromatic heterocyclic group containing one totwo nitrogen atoms” represents pyridyl group, pyridazinyl group,pyrimidinyl group and pyrazinyl group.

The term of “5 membered aromatic heterocyclic group containing one tofour nitrogen atoms” represents pyrrolyl group, pyrazolyl group,imidazolyl group, 1,2,4-triazolyl group, 1,2,3-triazolyl group, andtetrazolyl group.

The terms of “alkylsulfanyl”, “alkylsulfinyl”, and “alkylsulfonyl”represent an alkyl group containing a S(O)z moiety, respectively.

For example, example of the “alkylsulfanyl” when z is includesmethylsulfanyl group, ethylsulfanyl group, propylsulfanyl group, andisopropylsulfanyl group.

For example, example of the “alkylsulfinyl” when z is 1 includesmethylsulfinyl group, ethylsulfinyl group, propylsulfinyl group, andisopropylsulfinyl group.

For example, example of the “alkylsulfonyl” when z is includesmethylsulfonyl group, ethylsulfonyl group, propylsulfonyl group, andisopropylsulfonyl group.

Example of “N oxide compound” includes a compound represented by formula(I-N1), a compound represented by formula (I-N2), a compound representedby formula (I-N3), and a compound represented by formula (I-N4).

[wherein the symbols are the same as defined above.]

[wherein the symbols are the same as defined above.]

[wherein the symbols are the same as defined above.]

[wherein the symbols are the same as defined above.]

Examples of the Present compound include the following compounds.

A compound of the present invention wherein A¹ represents a nitrogenatom or a CR⁴, and R⁴ represents a hydrogen atom or a halogen atom;

A compound of the present invention wherein A¹ represents a nitrogenatom or a CH;

A compound of the present invention wherein R¹ represents a C2-C10haloalkyl group or a (C3-C7 cycloalkyl)C1-C3 alkyl group having one ormore substituents selected from Group G;

A compound of the present invention wherein R¹ represents a C2-C10haloalkyl group;

A compound of the present invention wherein R¹ represents a C2-C10 alkylgroup having two or more fluoro atoms;

A compound of the present invention wherein R¹ represents a C2-C6 alkylgroup having four or more fluoro atoms;

A compound of the present invention wherein R² represents a C1-C6 alkylgroup optionally having one or more halogen atoms;

A compound of the present invention wherein R² represents a C1-C6 alkylgroup;

A compound of the present invention wherein R² represents a methyl groupor an ethyl group;

A compound of the present invention wherein R² represents an ethylgroup;

A compound of the present invention wherein R³ represents independentlyof each other a C1-C6 chain hydrocarbon group optionally having one ormore substituents selected from Group B, a phenyl group optionallyhaving one or more substituents selected from Group D, a 5 or 6 memberedaromatic heterocyclic group optionally having one or more substituentsselected from Group D, a OR¹², a NR¹¹R¹², a NR^(11a)R^(12a), aS(O)_(y)R¹⁵, or a halogen atom;

A compound of the present invention wherein q represents 0, 1 or 2, andR³ represents independently of each other a C1-C6 chain hydrocarbongroup optionally having one or more substituents selected from Group B,a phenyl group optionally having one or more substituents selected fromGroup D, a 6 membered aromatic heterocyclic group selected from any oneof Group R (the 6 membered aromatic heterocyclic group may optionallyhave one or more substituents selected from Group D), a 5 memberedaromatic heterocyclic group selected from any one of Group Q (the 5membered aromatic heterocyclic group may optionally have one or moresubstituents selected from Group D), a OR¹², a NR¹¹R¹², aNR^(11a)R^(12a), a NR²⁹NR¹¹R¹², a S(O)_(y)R¹⁵, a C(O)OR¹⁷ or a halogenatom,

Group R:

A compound of the present invention wherein q represents 0, 1 or 2, andR³ represents independently of each other a C1-C6 chain hydrocarbongroup optionally having one or more substituents selected from Group B,a 5 membered aromatic heterocyclic group selected from any one of GroupQ (the 5 membered aromatic heterocyclic group may optionally have one ormore substituents selected from Group D), a OR¹², a NR¹¹R¹², aNR^(11a)R^(12a), a NR²⁹NR¹¹R¹², a S(O)_(y)R¹⁵, or a halogen atom,

Group Q:

{In the above formulae, R²⁶ represents a C1-C6 alkyl group optionallyhaving one or more halogen atoms};

A compound of the present invention wherein q represents 0, 1 or 2, andR³ represents independently of each other a C1-C6 chain hydrocarbongroup optionally having one or more halogen atoms, a phenyl groupoptionally having one or more substituents selected from Group D, a 6membered aromatic heterocyclic group containing one to two nitrogenatoms (the 6 membered aromatic heterocyclic group may optionally haveone or more substituents selected from Group D), a 5 membered aromaticheterocyclic group containing one to four nitrogen atoms (the 5 memberedaromatic heterocyclic group may optionally have one or more substituentsselected from Group D), a OR¹², a NR¹¹R¹², a NR²⁹NR¹¹R¹², a S(O)_(y)R¹⁵,or a halogen atom;

A compound of the present invention wherein R⁴ represents a hydrogenatom, or a halogen atom; R³ represents independently of each other aC1-C6 chain hydrocarbon group optionally having one or more halogenatoms, a phenyl group optionally having one or more substituentsselected from Group D, a 6 membered aromatic heterocyclic groupcontaining one to two nitrogen atoms (the 6 membered aromaticheterocyclic group may optionally have one or more substituents selectedfrom Group D), a 5 membered aromatic heterocyclic group containing oneto four nitrogen atoms (the 5 membered aromatic heterocyclic group mayoptionally have one or more substituents selected from Group D), aNR¹¹R¹², or a halogen atom;

A compound of the present invention wherein R⁴ represents a hydrogenatom, or a halogen atom; R³ represents independently of each other aC1-C6 chain hydrocarbon group optionally having one or more halogenatoms, a phenyl group optionally having one or more substituentsselected from Group D, a 6 membered aromatic heterocyclic group selectedfrom any one of the above-mentioned R-1 to R-9 (the 6 membered aromaticheterocyclic group may optionally have one or more substituents selectedfrom Group D), a 5 membered aromatic heterocyclic group selected fromany one of the above-mentioned Q-1 to Q-7 (the 5 membered aromaticheterocyclic group may optionally have one or more substituents selectedfrom Group D), a OR¹², a NR¹¹R¹², or a halogen atom;

A compound of the present invention wherein R⁴ represents a hydrogenatom, or a halogen atom; R³ represents independently of each other C1-C6chain hydrocarbon group optionally having one or more halogen atoms, aphenyl group optionally having one or more substituents selected fromGroup D, a OR¹², or a halogen atom;

A compound of the present invention wherein R³ represents independentlyof each other C1-C6 alkyl group optionally having one or more halogenatoms, a NR¹¹R¹², or a halogen atom; and R¹¹ and R¹² representindependently of each other a hydrogen atom or a C1-C3 alkyl groupoptionally having one or more halogen atoms;

A compound of the present invention wherein q represents 0, 1 or 2, andR³ represents independently of each other a C1-C6 alkyl group optionallyhaving one or more halogen atoms, or a halogen atom;

A compound of the present invention wherein q represents 0;

A compound of the present invention wherein R⁶ represents independentlyof each other a C1-C6 alkyl group optionally having one or more halogenatoms, or a halogen atom;

A compound of the present invention wherein p represents 0 or 1, and R⁶represents a C1-C6 alkyl group optionally having one or more halogenatoms, a OR¹², a NR¹⁸R¹⁹, a cyano group, a nitro group or a halogenatom;

A compound of the present invention wherein p represents 0 or 1, and R⁶represents a C1-C6 alkyl group optionally having one or more halogenatoms, or a halogen atom;

A compound of the present invention wherein p represents 0;

A compound of the present invention wherein R⁴ represents a hydrogenatom or a halogen atom, and R³ represents independently of each other aC1-C6 chain hydrocarbon group optionally having one or more halogenatoms, a 5 membered aromatic heterocyclic group containing 1 to 4nitrogen atoms, a NR¹¹R¹², or a halogen atom;

A compound of the present invention wherein R⁴ represents a hydrogenatom or a halogen atom, R¹ represents a C2-C10 haloalkyl group, R²represents a C2-C6 alkyl group optionally having one or more halogenatoms, and q represents 0, 1 or 2;

A compound of the present invention wherein

A¹ represents a nitrogen atom or a CH,

R¹ represents a C2-C10 haloalkyl group,

R² represents an ethyl group,

q represents 0, 1 or 2, R³ represents independently of each other aC1-C6 chain hydrocarbon group optionally having one or more substituentsselected from Group B, a 5 or 6 membered aromatic heterocyclic groupoptionally having one or more substituents selected from Group D, aOR¹², a NR¹¹R¹², a NR^(11a)R^(12a), a S(O)_(y)R¹⁵, or a halogen atom,and

R⁶ represents independently of each other a C1-C6 alkyl group optionallyhaving one or more halogen atoms, or a halogen atom;

A compound of the present invention wherein

A¹ represents a nitrogen atom or a CH,

R¹ represents a C2-C10 haloalkyl group,

R² represents an ethyl group,

q represents 0, 1 or 2,

R³ represents independently of each other a C1-C6 chain hydrocarbongroup optionally having one or more halogen atoms, a phenyl groupoptionally having one or more substituents selected from Group D, a 6membered aromatic heterocyclic group containing 1 to 2 nitrogen atoms(the 6 membered aromatic heterocyclic group may optionally have one ormore substituents selected from Group D), a 5 membered aromaticheterocyclic group containing 1 to 4 nitrogen atoms (the 5 memberedaromatic heterocyclic group may optionally have one or more substituentsselected from Group D), a OR¹², a NR¹¹R¹², a NR²⁹NR¹¹R¹², a S(O)_(y)R¹⁵,or a hydrogen atom, and

R⁶ represents independently of each other a C1-C6 alkyl group optionallyhaving one or more halogen atoms, or a halogen atom;

A compound of the present invention wherein

A¹ represents a nitrogen atom or a CH;

R¹ represents a C2-C10 haloalkyl group;

R² represents an ethyl group;

q represents 0, 1 or 2, R³ represents independently of each other aC1-C6 chain hydrocarbon group optionally having one or more halogenatoms, a phenyl group optionally having one or more substituentsselected from Group D, a 6 membered aromatic heterocyclic group selectedfrom any one of the above-mentioned R-1 to R-10 (the 6 membered aromaticheterocyclic group may optionally have one or more substituents selectedfrom Group D), a 5 membered aromatic heterocyclic group selected fromany one of the above-mentioned Q-1 to Q-15 (the 5 membered aromaticheterocyclic group may optionally have one or more substituents selectedfrom Group D), a OR¹², a NR¹¹R¹², a NR²⁹NR¹¹R¹², a S(O)_(y)R¹⁵, or ahydrogen atom, and

R⁶ represents independently of each other a C1-C6 alkyl group optionallyhaving one or more halogen atoms, or a halogen atom;

A compound of the present invention wherein

A¹ represents a nitrogen atom or a CH;

R¹ represents a C2-C10 alkyl group containing two or more fluoro atoms;

R² represents an ethyl group;

q represents 0 or 1, R³ represents a C1-C6 alkyl group optionally havingone or more halogen atoms or a halogen atom; and

p represents 0;

A compound of the present invention wherein

A¹ represents a nitrogen atom or a CH;

R¹ represents a C3-C6 alkyl group containing four or more fluoro atoms,

R² represents an ethyl group;

q represents 0, 1 or 2, R³ represents independently of each other aC1-C6 alkyl group optionally having one or more halogen atoms, a 5membered aromatic heterocyclic group selected from any one of Group Q(the 5 membered aromatic heterocyclic group may optionally have one ormore substituents selected from Group D), a OR¹², a NR¹¹R¹², aNR^(11a)R^(12a) or a halogen atom; and

R⁶ represents of independently of each other a C1-C6 alkyl groupoptionally having one or more halogen atoms or a halogen atom;

A compound of the present invention wherein

A¹ represents a nitrogen atom or a CH;

R¹ represents a C3-C6 alkyl group containing four or more fluoro atoms;

R² represents an ethyl group;

q represents 0, 1 or 2, R³ represents independently of each other aC1-C6 chain hydrocarbon group optionally having one or more halogenatoms, a phenyl group optionally having one or more substituentsselected from Group D, a 6 membered aromatic heterocyclic groupcontaining one to two nitrogen atoms (the 6 membered aromaticheterocyclic group may optionally have one or more substituents selectedfrom Group D), a 5 membered aromatic heterocyclic group containing 1 to4 nitrogen atoms (the a 5 membered aromatic heterocyclic group mayoptionally have one or more substituents selected from Group D), a OR¹²,a NR¹¹R¹², a NR²⁹NR¹¹R¹², a S(O)_(y)R¹⁵ or a halogen atom; and

R⁶ represents independently of each other a C1-C6 alkyl group optionallyhaving one or more halogen atoms or a halogen atom;

A compound of the present invention wherein

A¹ represents a nitrogen atom or a CH;

R¹ represents a C3-C6 alkyl group containing four or more fluoro atoms;

R² represents an ethyl group;

q represents 0, 1 or 2, R³ represents independently of each other aC1-C6 chain hydrocarbon group optionally having one or more halogenatoms, a phenyl group optionally having one or more substituentsselected from Group D, a 6 membered aromatic heterocyclic group selectedfrom any one of the above-mentioned R-1 to R-10 (the 6 membered aromaticheterocyclic group may optionally have one or more substituents selectedfrom Group D), a 5 membered aromatic heterocyclic group selected fromany one of the above-mentioned Q-1 to Q-15 (the 5 membered aromaticheterocyclic group may optionally have one or more substituents selectedfrom Group D), a OR¹², a NR¹¹R¹², a NR²⁹NR¹¹R¹², a S(O)_(y)R¹⁵, or ahalogen atom; and

R⁶ represents independently of each other a C1-C6 alkyl group optionallyhaving one or more halogen atoms or a halogen atom;

A compound of the present invention wherein

A¹ represents a nitrogen atom or a CH;

R¹ represents a C3-C6 haloalkyl group containing 4 or more fluoro atoms;

R² represents an ethyl group;

q represents 0; and

p represents 0;

A compound of the present invention wherein

R¹ represents a C2-C10 alkyl group having one or more halogen atoms, aC3-C10 alkenyl group having one or more halogen atoms, a (C1-C5alkoxy)C2-C5 alkyl group having one or more halogen atoms, a (C1-C5alkylsulfanyl)C2-C5 alkyl group having one or more halogen atoms, a(C1-C5 alkylsulfinyl)C2-C5 alkyl group having one or more halogen atoms,a (C1-C5 alkylsulfonyl)C2-C5 alkyl group having one or more halogenatoms, or a (C3-C7 cycloalkyl)C1-C3 alkyl group having one or morehalogen atoms; R² represents a C1-C6 alkyl group, q represents 0 or 1;R³ represents a C1-C6 alkyl group optionally having one or more halogenatoms; and p represents 0.

A compound represented by formula (I-A):

(hereinafter referred to as Present compound (I-A))[wherein the symbols are the same as defined above].

A Present compound (I-A) wherein

R¹ represents a C2-C10 alkyl group having one or more halogen atoms, aC3-C10 alkenyl group having one or more halogen atoms, a (C1-C5alkoxy)C2-C5 alkyl group having one or more halogen atoms, a (C1-C5alkylsulfanyl)C2-C5 alkyl group having one or more halogen atoms, a(C1-C5 alkylsulfinyl)C2-C5 alkyl group having one or more halogen atoms,a (C1-C5 alkylsulfonyl)C2-C5 alkyl group having one or more halogenatoms, or a (C3-C7 cycloalkyl)C1-C3 alkyl group having one or morehalogen atoms; R² represents a C1-C6 alkyl group, q represents 0 or 1;and R³ represents independently of each other a C1-C6 chain hydrocarbongroup optionally having one or more halogen atoms, a phenyl groupoptionally having one or more substituents selected from Group D, a 6membered aromatic heterocyclic group selected from any one of theabove-mentioned R-1 to R-9 (the 6 membered aromatic heterocyclic groupmay optionally have one or more substituents selected from Group D), a 5membered aromatic heterocyclic group selected from any one of theabove-mentioned Q-1 to Q-7 (the 5 membered aromatic heterocyclic groupmay optionally have one or more substituents selected from Group D), aOR¹², a NR¹¹R¹², or a halogen atom; and p represents 0;

A Present compound (I-A) wherein

R¹ represents a C2-C10 alkyl group having one or more halogen atoms, aC3-C10 alkenyl group having one or more halogen atoms, a (C1-C5alkoxy)C2-C5 alkyl group having one or more halogen atoms, a (C1-C5alkylsulfanyl)C2-C5 alkyl group having one or more halogen atoms, a(C1-C5 alkylsulfinyl)C2-C5 alkyl group having one or more halogen atoms,a (C1-C5 alkylsulfonyl)C2-C5 alkyl group having one or more halogenatoms, or a (C3-C7 cycloalkyl)C1-C3 alkyl group having one or morehalogen atoms; R² represents a C1-C6 alkyl group, q represents 0 or 1;R³ represents independently of each other a C1-C6 chain hydrocarbongroup optionally having one or more halogen atoms, a phenyl groupoptionally having one or more substituents selected from Group D, a 6membered aromatic heterocyclic group selected from any one of theabove-mentioned R-1 to R-9 (the 6 membered aromatic heterocyclic groupmay optionally have one or more substituents selected from Group D), a 5membered aromatic heterocyclic group selected from any one of theabove-mentioned Q-1 to Q-7 (the 5 membered aromatic heterocyclic groupmay optionally have one or more substituents selected from Group D), aOR¹², a NR¹¹R¹², or a halogen atom; and p represents 0;

A Present compound (I-A) wherein

R¹ represents a C2-C10 alkyl group having one or more halogen atoms, aC3-C10 alkenyl group having one or more halogen atoms, a (C1-C5alkoxy)C2-C5 alkyl group having one or more halogen atoms, a (C1-C5alkylsulfanyl)C2-C5 alkyl group having one or more halogen atoms, a(C1-C5 alkylsulfinyl)C2-C5 alkyl group having one or more halogen atoms,a (C1-C5 alkylsulfonyl)C2-C5 alkyl group having one or more halogenatoms, or a (C3-C7 cycloalkyl)C1-C3 alkyl group having one or morehalogen atoms; R² represents a C1-C6 alkyl group, q represents 0 or 1;R³ represents independently of each other C1-C6 chain hydrocarbon groupoptionally having one or more halogen atoms, a phenyl group optionallyhaving one or more substituents selected from Group D, a 6 memberedaromatic heterocyclic group selected from any one of the above-mentionedR-1 to R-9 (the 6 membered aromatic heterocyclic group may optionallyhave one or more substituents selected from Group D), a OR¹², a NR¹¹R¹²,or a halogen atom; and p represents 0;

A Present compound (I-A) wherein

R¹ represents a C2-C10 alkyl group having one or more halogen atoms, aC3-C10 alkenyl group having one or more halogen atoms, a (C1-C5alkoxy)C2-C5 alkyl group having one or more halogen atoms, a (C1-C5alkylsulfanyl)C2-C5 alkyl group having one or more halogen atoms, a(C1-C5 alkylsulfinyl)C2-C5 alkyl group having one or more halogen atoms,a (C1-C5 alkylsulfonyl)C2-C5 alkyl group having one or more halogenatoms, or a (C3-C7 cycloalkyl)C1-C3 alkyl group having one or morehalogen atoms; R² represents a C1-C6 alkyl group, q represents 0 or 1,R³ represents a C1-C6 alkyl group optionally having one or more halogenatoms; and p represents 0.

A Present compound (I-A) wherein

R¹ represents a C2-C10 haloalkyl group, and

R² represents a C1-C6 alkyl group optionally having one or more halogenatoms;

A Present compound (I-A) wherein

R¹ represents a C2-C10 haloalkyl group or a (C3-C7 cycloalkyl)C1-C3alkyl group having one or more halogen atoms; R² represents a C1-C6alkyl group; q represents 0 or 1; R³ represents a C1-C6 alkyl groupoptionally having one or more halogen atoms; and p represents 0.

A Present compound (I-A) wherein

R¹ represents a C2-C10 haloalkyl group;

R² represents an ethyl group;

R³ represents independently of each other a C1-C6 chain hydrocarbongroup optionally having one or more substituents selected from Group B,a 5 or 6 membered aromatic heterocyclic group optionally having one ormore substituents selected from Group D, a OR¹², a NR¹¹R¹², aNR^(11a)R^(12a), a S(O)_(y)R¹⁵, a halogen atom; and

R⁶ represents independently of each other a C1-C6 alkyl group optionallyhaving one or more halogen atoms, or a halogen atom.

A Present compound (I-A) wherein

R¹ represents a C2-C10 haloalkyl group;

R² represents an ethyl group;

q represents 0, 1 or 2;

R³ represents independently of each other a C1-C6 chain hydrocarbongroup optionally having one or more halogen atoms, a phenyl groupoptionally having one or more substituents selected from Group D, a 6membered aromatic heterocyclic group containing one to two nitrogenatoms (the 6 membered aromatic heterocyclic group may optionally haveone or more substituents selected from Group D), a 5 membered aromaticheterocyclic group containing 1 to 4 nitrogen atoms (the 5 memberedaromatic heterocyclic group may optionally have one or more substituentsselected from Group D), a OR¹², a NR¹¹R¹², a NR²⁹ _(NR) ¹¹R¹², aS(O)_(y)R¹⁵, or a halogen atom; and

R⁶ represents independently of each other a C1-C6 alkyl group optionallyhaving one or more halogen atoms or a halogen atom.

A Present compound (I-A) wherein

R¹ represents a C2-C10 haloalkyl group;

R² represents an ethyl group;

q represents 0, 1 or 2, R³ represents independently of each other aC1-C6 chain hydrocarbon group optionally having one or more halogenatoms, a phenyl group optionally having one or more substituentsselected from Group D, a 6 membered aromatic heterocyclic group selectedfrom any one of the above-mentioned R-1 to R-10 (the 6 membered aromaticheterocyclic group may optionally have one or more substituents selectedfrom Group D), a 5 membered aromatic heterocyclic group selected fromany one of the above-mentioned Q-1 to Q-15 (the 5 membered aromaticheterocyclic group may optionally have one or more substituents selectedfrom Group D), a OR¹², a NR¹¹R¹², a NR²⁹NR¹¹R¹², a S(O)_(y)R¹⁵, or ahalogen atom; and

R⁶ represents independently of each other a C1-C6 alkyl group optionallyhaving one or more halogen atoms or a halogen atom.

A Present compound (I-A) wherein

R¹ represents a C2-C10 alkyl group having two or more fluoro atoms,

R² represents an ethyl group;

R³ represents independently of each other a C1-C6 alkyl group optionallyhaving one or more halogen atoms or a halogen atom; and

p represents 0.

A Present compound (I-A) wherein

R¹ represents a C3-C6 alkyl group containing four or more fluoro atoms;

R² represents an ethyl group;

R³ represents independently of each other a C1-C6 alkyl group optionallyhaving one or more halogen atoms, a 5 membered aromatic heterocyclicgroup selected from any one of Group Q (the 5 membered aromaticheterocyclic group may optionally have one or more substituents selectedfrom Group D), a OR¹², a NR¹¹R¹², a NR^(11a)R^(12a), or a halogen atom;and

R⁶ represents independently of each other a C1-C6 alkyl group optionallyhaving one or more halogen atoms or a halogen atom.

A Present compound (I-A) wherein

R¹ represents a C3-C6 haloalkyl group containing 4 or more fluoro atoms,R² represents an ethyl group; q represents 0; and p represents 0.

A compound of the present invention wherein A¹ represents a CR⁴; and R⁴represents a hydrogen atom or a halogen atom;

A compound of the present invention wherein A¹ represents a CH;

A compound represented by formula (I-B):

(hereinafter referred to as Present compound (I-B))[wherein the symbols are the same as defined above.]

A Present compound (I-B) wherein

R⁴ represents a hydrogen atom or a halogen atom; R¹ represents a C2-C10alkyl group having one or more halogen atoms, a C3-C10 alkenyl grouphaving one or more halogen atoms, a (C1-C5 alkoxy)C2-C5 alkyl grouphaving one or more halogen atoms, a (C1-C5 alkylsulfanyl)C2-C5 alkylgroup having one or more halogen atoms, a (C1-C5 alkylsulfinyl)C2-C5alkyl group having one or more halogen atoms, a (C1-C5alkylsulfonyl)C2-C5 alkyl group having one or more halogen atoms, or a(C3-C7 cycloalkyl)C1-C3 alkyl group having one or more halogen atoms; R²represents a C1-C6 alkyl group; q represents 0 or 1; R³ representsindependently of each other a C1-C6 chain hydrocarbon group optionallyhaving one or more halogen atoms, a phenyl group optionally having oneor more substituents selected from Group D, a 6 membered aromaticheterocyclic group selected from any one of the above-mentioned R-1 toR-9 (the 6 membered aromatic heterocyclic group may optionally have oneor more substituents selected from Group D), a 5 membered aromaticheterocyclic group selected from any one of the above-mentioned Q-1 toQ-7 (the 5 membered aromatic heterocyclic group may optionally have oneor more substituents selected from Group D), a OR¹², a NR¹¹R¹², or ahalogen atom; and p represents 0;

A Present compound (I-B) wherein

R⁴ represents a hydrogen atom or a halogen atom; R¹ represents a C2-C10alkyl group having one or more halogen atoms, a C3-C10 alkenyl grouphaving one or more halogen atoms, a (C1-C5 alkoxy)C2-C5 alkyl grouphaving one or more halogen atoms, a (C1-C5 alkylsulfanyl)C2-C5 alkylgroup having one or more halogen atoms, a (C1-C5 alkylsulfinyl)C2-C5alkyl group having one or more halogen atoms, a (C1-C5alkylsulfonyl)C2-C5 alkyl group having one or more halogen atoms, or a(C3-C7 cycloalkyl)C1-C3 alkyl group having one or more halogen atoms; R²represents a C1-C6 alkyl group; q represents 0 or 1; R³ represents aC1-C6 alkyl group; q represents 0 or 1; R³ represents independently ofeach other a C1-C6 chain hydrocarbon group optionally having one or morehalogen atoms, a phenyl group optionally having one or more substituentsselected from Group D, a 6 membered aromatic heterocyclic group selectedfrom any one of the above-mentioned R-1 to R-9 (the 6 membered aromaticheterocyclic group may optionally have one or more substituents selectedfrom Group D), a OR¹², a NR¹¹R¹², or a halogen atom; and p represents 0;

A Present compound (I-B) wherein

R⁴ represents a hydrogen atom or a halogen atom; R¹ represents a C2-C10alkyl group having one or more halogen atoms, a C3-C10 alkenyl grouphaving one or more halogen atoms, a (C1-C5 alkoxy)C2-C5 alkyl grouphaving one or more halogen atoms, a (C1-C5 alkylsulfanyl)C2-C5 alkylgroup having one or more halogen atoms, a (C1-C5 alkylsulfinyl)C2-C5alkyl group having one or more halogen atoms, a (C1-C5alkylsulfonyl)C2-C5 alkyl group having one or more halogen atoms, or a(C3-C7 cycloalkyl)C1-C3 alkyl group having one or more halogen atoms; R²represents a C1-C6 alkyl group; q represents 0 or 1; R³ represents aC1-C6 alkyl group optionally having one or more halogen atoms;

and p represents 0.

A Present compound (I-B) wherein

R⁴ represents a hydrogen atom or a halogen atom;

R¹ represents a C2-C10 haloalkyl group; and

R² represents a C1-C6 alkyl group optionally having one or more halogenatoms.

A Present compound (I-B) wherein

R¹ represents a C2-C10 haloalkyl group; q represents 0 or 1; R³represents a C1-C6 alkyl group optionally having one or more halogenatoms; and p represents 0.

A Present compound (I-B) wherein

R⁴ represents a hydrogen atom or a halogen atom;

R¹ represent a C2-C10 haloalkyl group;

R³ represents independently of each other a C1-C6 chain hydrocarbongroup optionally having one or more substituents selected from Group B,a 5 or 6 membered aromatic heterocyclic group optionally having one ormore substituents selected from Group D, a OR¹², a NR¹¹R¹², aNR^(11a)R^(12a), a S(O)_(y)R¹⁵, or a halogen atom; and

R⁶ represents independently of each other a C1-C6 alkyl group optionallyhaving one or more halogen atoms or a halogen atom.

A Present compound (I-B) wherein

R⁴ represents a hydrogen atom or a halogen atom;

R¹ represents a C2-C10 haloalkyl group;

R² represents an ethyl group;

q represents 0, 1 or 2, R³ represents independently of each other aC1-C6 chain hydrocarbon group optionally having one or more halogenatoms, a phenyl group optionally having one or more substituentsselected from Group D, a 6 membered aromatic heterocyclic groupcontaining one to two nitrogen atoms (the 6 membered aromaticheterocyclic group may optionally have one or more substituents selectedfrom Group D), a 5 membered aromatic heterocyclic group containing 1 to4 nitrogen atoms (the 5 membered aromatic heterocyclic group mayoptionally have one or more substituents selected from Group D), a OR¹²,a NR¹¹R¹², a NR²⁹R¹¹R¹², a S(O)_(y)R¹⁵, or a halogen atom; and

R⁶ represents independently of each other a C1-C6 alkyl group optionallyhaving one or more halogen atoms or a hydrogen atom.

A Present compound (I-B) wherein

R⁴ represents a hydrogen atom or a halogen atom;

R¹ represents a C2-C10 haloalkyl group;

R² represents an ethyl group;

q represents 0, 1 or 2, R³ represents independently of each other aC1-C6 chain hydrocarbon group optionally having one or more halogenatoms, a phenyl group optionally having one or more substituentsselected from Group D, a 6 membered aromatic heterocyclic group selectedfrom any one of the above-mentioned R-1 to R-10 (the 6 membered aromaticheterocyclic group may optionally have one or more substituents selectedfrom Group D), a 5 membered aromatic heterocyclic group selected fromany one of the above-mentioned Q-1 to Q-15 (the 5 membered aromaticheterocyclic group may optionally have one or more substituents selectedfrom Group D), a OR¹², a NR¹¹R¹², a NR²⁹R¹¹R¹², a S(O)_(y)R¹⁵, or ahalogen atom; and

R⁶ represents independently of each other a C1-C6 alkyl group optionallyhaving one or more halogen atoms or a halogen atom.

A Present compound (I-B) wherein

R⁴ represents a hydrogen atom;

R¹ represents a C2-C10 alkyl group having two or more fluoro atoms;

R² represents an ethyl group;

R³ represents independently of each other a C1-C6 alkyl group optionallyhaving one or more halogen atoms or a halogen atom; and p represents 0.

A Present compound (I-B) wherein

R⁴ represents a hydrogen atom;

R¹ represents a C3-C6 alkyl group containing four or more fluoro atoms;

R² represents an ethyl group;

R³ represents independently of each other a C1-C6 alkyl group optionallyhaving one or more halogen atoms, a 5 membered aromatic heterocyclicgroup selected from any one of Group Q (the 5 membered aromaticheterocyclic group may optionally have one or more substituents selectedfrom Group D), a OR¹², a NR¹¹R¹², a NR^(11a)R^(12a), or a hydrogen atom;and

R⁶ represents independently of each other a C1-C6 alkyl group optionallyhaving one or more halogen atoms or a hydrogen atom.

A Present compound (I-B) wherein

R¹ represents a C3-C6 haloalkyl group containing 4 or more fluoro atoms;

R² represents an ethyl group;

q represents 1, R³ represents a C1-C6 alkyl group optionally having oneor more halogen atoms; and

p represents 0.

Next, a process for preparing the compound of the present invention isexplained.

The compound of the present invention can be prepared, for example,according to the following processes.

Process 1

A compound represented by formula (Ib) (hereinafter, referred to asPresent compound (Ib)) and a compound represented by formula (Ic)(hereinafter, referred to as Present compound (Ic)) may be prepared byreacting a compound represented by formula (Ia) (hereinafter, referredto as Present compound (Ia)) with an oxidizing agent.

[wherein the symbols are the same as defined above]

First, a process for preparing the Present compound (Ib) from thePresent compound (Ia) is described.

The reaction is usually carried out in a solvent. Examples of thesolvent to be used in the reaction include halogenated aliphatichydrocarbons such as dichloromethane and chloroform (hereinafter,collectively referred to as halogenated aliphatic hydrocarbons);nitriles such as acetonitrile (hereinafter collectively referred tonitriles); esters such as ethyl acetate (hereinafter collectivelyreferred to esters); alcohols such as methanol and ethanol (hereinafter,collectively referred to as alcohols); acetic acid; water; and mixedsolvents thereof.

Examples of the oxidizing agent to be used in the reaction includessodium periodate, m-chloroperoxybenzoic acid (hereinafter referred to asmCPBA), and hydrogen peroxide.

When hydrogen peroxide is used as the oxidizing agent, sodium carbonateor a catalyst may be added as needed.

Examples of the catalyst to be used in the reaction include tungsticacid, and sodium tungstate.

In the reaction, the oxidizing agent is used usually within a range of 1to 1.2 molar ratio(s), the sodium carbonate is used usually within arange of 0.01 to 1 molar ratio(s), and the catalyst is used usuallywithin a range of 0.01 to 0.5 molar ratios, as opposed to 1 mole of thePresent compound (Ia).

The reaction temperature of the reaction is usually within a range of−20 to 80° C. The reaction period of the reaction is usually within arange of 0.1 to 12 hours.

When the reaction is completed, to the reaction mixtures is added water,and the reaction mixtures are then extracted with organic solvent(s),and the organic layers are washed successively with an aqueous solutionof a reducing agent (such as sodium sulfite, and sodium thiosulfate) andan aqueous solution of a base (such as sodium hydrogen carbonate). Theresulting organic layers are dried and concentrated to give the Presentcompound (Ib).

Next, a process for preparing the Present compound (Ic) from the Presentcompound (Ib) is explained.

The reaction is usually carried out in a solvent. Examples of thesolvent to be used in the reaction include halogenated aliphatichydrocarbons, nitriles, alcohols, acetic acid, water, and mixed solventsthereof.

Examples of the oxidizing agent to be used in the reaction include mCPBAand hydrogen peroxide. When hydrogen peroxide is used as oxidizingagent, a base or a catalyst may be added as needed.

Examples of the base to be used include sodium carbonate.

Examples of the catalyst to be used include sodium tungstate.

In the reaction, the oxidizing agent is used usually within a range of 1to 2 molar ratio(s), the base is used usually within a range of 0.01 to1 molar ratio(s), and the catalyst is used usually within a range of0.01 to 0.5 molar ratios, as opposed to 1 mole of the Present compound(Ib).

The reaction temperature of the reaction is usually within a range of−20 to 120° C. The reaction period of the reaction is usually within arange of 0.1 to 12 hours.

When the reaction is completed, to the reaction mixtures is added water,and the reaction mixtures are then extracted with organic solvent(s),and the organic layers are washed successively with an aqueous solutionof a reducing agent (such as sodium sulfite, and sodium thiosulfate) andan aqueous solution of a base (such as sodium hydrogen carbonate). Theresulting organic layers are dried and concentrated to give the Presentcompound (Ic).

Also, the Present compound (Ic) may be prepared in one step (one-spot)by reacting the Present compound (Ia) with an oxidizing agent.

The reaction may be carried out by using the oxidizing agent usually in2.0 to 2.4 molar ratios as opposed to 1 mole of the Present compound(Ia) according to the method for preparing the Present compound (Ic)from the Present compound (Ib).

Process 2

The compound of the present invention represented by formula (I)(hereinafter referred to as Present compound (I)) may be prepared byreacting a compound represented by formula (M-3) (hereinafter referredto as Compound (M-3)) with a compound represented by formula (R-3)(hereinafter, referred to as Compound (R-3)) in the presence of a base.

[wherein V¹ represents a halogen atom, a trifluoromethansulfonyloxygroup, a nonafluorobutanesulfonyloxy group, or a tosyloxy group, and theother symbols are the same as defined above.]

The reaction is usually carried out in a solvent. Examples of thesolvent to be used in the reaction include ethers such astetrahydrofuran (hereinafter, referred to as THF), ethyleneglycoldimethyl ether, methyl tert-butyl ether, and 1,4-dioxane (hereinafter,collectively referred to as ethers); halogenated aliphatic hydrocarbons;aromatic hydrocarbons such as toluene and xylene (hereinafter,collectively referred to as aromatic hydrocarbons); polar aproticsolvents such as dimethylformamide (hereinafter, referred to as DMF),N-methyl pyrrolidone (hereinafter, referred to as NMP), dimethylsulfoxide (hereinafter, referred to DMSO) (hereinafter, collectivelyreferred to as polar aprotic solvent); and mixed solvents thereof.

Examples of the base to be used in the reaction include organic basessuch as triethylamine, diisopropylethylamine, pyridine,4-(dimethylamino)pyridine (hereinafter, collectively referred to asorganic bases); alkali metal hydrides such as sodium hydride(hereinafter, collectively referred to as alkali metal hydrides); andalkali metal carbonates such as sodium carbonate and potassium carbonate(hereinafter, referred to as alkali metal carbonates).

In the reaction, the compound (R-3) is usually used within a range of in1 to 10 molar ratio(s), and the base is usually used within a range of0.1 to 5 molar ratio(s), as opposed to 1 mole of the compound (M-3).

The reaction temperature is usually within a range of −20 to 150° C. Thereaction period of the reaction is usually within a range of 0.5 to 24hours.

When the reaction is completed, to the reaction mixtures is added water,and the reaction mixtures are then extracted with organic solvents, andthe resulting organic layers are worked up (for example, drying andconcentration) to give the Present compound (I).

Process 3

The Present compound (Ia) may be prepared by reacting a compoundrepresented by formula (M-1) (hereinafter, referred to Compound (M-1))with a compound represented by formula (R-1) (hereinafter, referred toCompound (R-1)) in the presence of a base.

[wherein V² represents a halogen atom, and the other symbols are thesame as defined above.]

The reaction is usually carried out in a solvent. Examples of thesolvent to be used in the reaction include ethers, aromatichydrocarbons, nitriles, polar aprotic solvents, and mixed solventsthereof.

Examples of the base to be used in the reaction include alkali metalcarbonates and alkali metal hydrides.

In the reaction, the compound (R-1) is used usually within a range of 1to 10 molar ratio(s), and the base is used usually within a range of 1to 10 molar ratio(s), as opposed to 1 mole of the compound (M-1).

The reaction temperature is usually within a range of −20 to 150° C. Thereaction period of the reaction is usually within a range of 0.5 to 24hours.

When the reaction is completed, the reaction mixtures are extracted withorganic solvents, and the resulting organic layers are worked up (forexample, drying and concentration) to give the Present compound (Ia).

V² is preferably a fluorine atom or a chlorine atom.

Process 4

The Present compound (I) may be prepared by reacting a compoundrepresented by formula (M-4) (hereinafter, referred to as Compound(M-4)) with a compound represented by formula (R-4) (hereinafter,referred to as Compound (R-4)) in the presence of a base.

[wherein the symbols are the same as defined above.]

The reaction is usually carried out in a solvent. Examples of thesolvent to be used in the reaction include ethers, aromatichydrocarbons, nitriles, polar aprotic solvent, and mixed solventsthereof.

Examples of the base to be used in the reaction include alkali metalcarbonates and alkali metal hydrides.

In the reaction, the compound (R-4) is usually used within a range of 1to 10 molar ratio(s), and the base is usually used within a range of 1to 10 molar ratio(s), as opposed to 1 mole of the compound (M-4).

The reaction temperature is usually within a range of −20 to 150° C. Thereaction period of the reaction is usually within a range of 0.5 to 24hours.

When the reaction is completed, to the reaction mixtures is added water,and the reaction mixtures are then extracted with organic solvents, andthe resulting organic layers are worked up (for example, drying andconcentration) to give the Present compound (I).

V is preferably a fluorine atom.

Process 5

A compound represented by formula (Ig) (hereinafter, referred to asPresent compound (Ig)) may be prepared according to a method describedbelow.

[wherein R³⁷ represents a C1-C6 alkyl group, R35 represents a hydrogenatom, a C1-C6 alkyl group optionally having one or more halogen atoms, aphenyl group optionally having one or more substituents selected fromGroup D, or a 5 or 6 membered aromatic heterocyclic group optionallyhaving one or more substituents selected from Group D, and the othersymbols are the same as defined above.]

First, Step 1 is explained.

In the Step 1, a compound represented by formula (M-7) (hereinafter,referred to as Compound (M-7)) and a compound represented by formula(R-7) (hereinafter, referred to as Compound (R-7)) are reacted.

The compound (R-7) may be prepared according to a similar method to thatdescribed in International Publication No. 2009/054742.

The reaction is usually carried out in a solvent. Examples of thesolvent to be used in the reaction include ethers, aliphatichydrocarbons, aromatic hydrocarbons, halogenated aliphatic hydrocarbons,alcohols, esters, nitriles, polar aprotic solvent, nitrogen-containingaromatic compounds such as pyridine and 2,6-lutidine (hereinafter,collectively referred to as nitrogen-containing aromatic compounds), andmixed solvents thereof.

A base may be added to the reaction, and examples of the base includeorganic bases.

In the reaction, the compound (R-7) is usually used within a range of 1to 10 molar ratio(s), and the base is usually used within a range of 1to 10 molar ratio(s), as opposed to 1 mole of the compound (M-7)).

The reaction temperature is usually within a range of −50 to 200° C. Thereaction period of the reaction is usually within a range of 0.1 to 24hours.

When the reaction is completed, the reaction mixtures are concentratedto obtain the residues, which are used as itself in the Step 2.Alternatively, to the reaction mixtures are added water and the mixturesare then extracted with organic solvents, and the organic layers areworked (for example, drying and concentration) to obtain the residues,which are used in the Step 2.

Next, Step 2 is explained.

In the Step 2, the residue obtained in the step 1 is reacted withammonia to give the Present compound (Ig).

The reaction is usually carried out in a solvent.

Examples of the solvent to be used in the reaction include ethers,nitriles, alcohols, polar aprotic solvent, nitrogen-containing aromaticcompounds, and mixed solvents thereof.

Examples of the ammonia to be used in the reaction include aqueousammonia solution and solution of ammonia in methanol.

In the reaction, ammonia is usually used within a range of 1 to 100molar ratio(s) as opposed to 1 mole of the compound (M-7).

The reaction temperature is usually within a range of 0 to 100° C. Thereaction period of the reaction is usually within a range of 0.1 to 24hours.

When the reaction is completed, to the reaction mixtures is added water,and the resulting mixtures are extracted with organic solvents, and theorganic layers are worked up (for example, drying and concentration) togive the Present compound (Ig).

Process 6

A compound represented by formula (Id) (hereinafter, referred to asPresent compound (Id)), a compound represented by formula (Ie)(hereinafter, referred to Present compound (Ie)), a compound representedby formula (If) (hereinafter, referred to Present compound (If)), and acompound represented by formula (Im) (hereinafter, referred to Presentcompound (Im) may be prepared by reacting the Present compound (Ic) withan oxidizing agent.

[wherein the symbols are the same as defined above.]

The reaction is usually carried out in a solvent. Examples of thesolvent to be used in the reaction include halogenated aliphatichydrocarbons; nitriles; esters such as ethyl acetate; alcohols; aceticacid; water; and mixed solvents thereof.

Examples of the oxidizing agent to be used in the reaction include mCPBAand hydrogen peroxide.

When hydrogen peroxide is used as the oxidizing agent, an acid, a baseor a catalyst may be added as needed.

Examples of the acid to be used in the reaction include acetic acid,sulfuric acid, and trifluoroacetic acid.

Examples of the base to be used include sodium carbonate.

Examples of the catalyst to be used include tungstic acid and sodiumtungstate.

In the reaction, the oxidizing agent is used usually within a range of 1to 10 molar ratio(s), the acid is used usually within a range of 0.01 to1 molar ratio(s), the base is used usually within a range of 0.01 to 1molar ratio(s), and the catalyst is used usually within a range of 0.01to 0.5 molar ratio(s), as opposed to 1 mole of the Present compound(Ic).

The reaction temperature of the reaction is usually within a range of−20 to 80° C. The reaction period of the reaction is usually within arange of 0.1 to 24 hours.

When the reaction is completed, to the reaction mixtures is added water,and the reaction mixtures are then extracted with organic solvent(s),and the organic layers are washed with an aqueous solution of a reducingagent (such as sodium sulfite, and sodium thiosulfate) and an aqueoussolution of a base (such as sodium hydrogen carbonate). The resultingorganic layers are dried and concentrated to give the residues, and theresulting residues are worked up (such as chromatography orrecrystallization) to isolate the Present compound (Id), the Presentcompound (Ie) and the Present compound (If), or the Present compound(Im) respectively.

Process 7

The Present compound (Ia) may be prepared by reacting a compoundrepresented by formula (M-2) (hereinafter, referred to as Compound(M-2)) with a compound represented by formula (R-2) (hereinafter,referred to as Compound (R-2)) in the presence of a base.

[wherein the symbols are the same as defined above.]

The reaction is usually carried out in a solvent. Examples of thesolvent to be used in the reaction include ethers, aromatichydrocarbons, nitriles, and polar aprotic solvent.

Examples of the base to be used in the reaction include alkali metalcarbonates and alkali metal hydrides.

In the reaction, the compound (R-2) is usually used within a range of in1 to 10 molar ratio(s), and the base is usually used within a range of 1to 10 molar ratio(s), as opposed to 1 mole of the compound (M-2).Preferably, the compound (R-2) is usually used within a range of in 1.0to 1.1 molar ratio(s), and the base is usually used within a range of 1to 2 molar ratio(s), as opposed to 1 mole of the compound (M-2).

The reaction temperature is usually within a range of −20 to 150° C. Thereaction period of the reaction is usually within a range of 0.5 to 24hours.

When the reaction is completed, to the reaction mixtures is added water,and the reaction mixtures are then extracted with organic solvents, andthe resulting organic layers are worked up (for example, drying andconcentration) to give the Present compound (Ia).

Process 8

A compound represented by formula (Ik) (hereinafter, referred to asPresent compound (Ik)) may be prepared according to a method describedbelow.

[wherein R³⁴ and R³⁶ represent independently of each other a hydrogenatom, a C1-C6 alkyl group optionally having one or more halogen atoms, aphenyl group optionally having one or more substituents selected fromGroup D, or a 5 or 6 membered aromatic heterocyclic group optionallyhaving one or more substituents selected from Group D; R^(y) representsa hydrogen atom, or a C1-C4 alkyl group; and the other symbols are thesame as defined above.]

First, Step 1 is explained.

In the Step 1, a compound represented by formula (M-20) (hereinafter,referred to as Compound (M-20)) and a compound represented by formula(R-5) (hereinafter, referred to as Compound (R-5)) are reacted to give acompound represented by formula (M-22a) (hereinafter, referred to asCompound (M-22a)) and a compound represented by formula (M-22b)(hereinafter, referred to as Compound (M-22b)).

The reaction is usually carried out in a solvent. Examples of thesolvent to be used in the reaction include ethers, aliphatichydrocarbons, aromatic hydrocarbons, halogenated aliphatic hydrocarbons,alcohols, esters, nitriles, polar aprotic solvent, nitrogen-containingaromatic compounds, and mixed solvents thereof.

An acid or a base may be added to the reaction as needed. Examples ofthe acid to be used in the reaction include carbonic acids such asacetic acid; and sulfonic acids such as methanesulfonic acid andp-toluenesulfonic acid, and examples of the base to be used in thereaction include alkali metal carbonates, alkali metal hydrides, andorganic bases.

In the reaction, the compound (R-5) is usually used within a range of 1to 10 molar ratio(s), and the base is usually used within a range of 0.1to 10 molar ratio(s), as opposed to 1 mole of the compound (M-20).

The reaction temperature is usually within a range of 0 to 200° C. Thereaction period of the reaction is usually within a range of 0.1 to 24hours.

When the reaction is completed, to the reaction mixtures is added water,and the reaction mixtures are then extracted with organic solvents, andthe reaction mixtures are worked up (for example, drying andconcentration) to give the Present compound (M-22a), the Presentcompound (M-22b), or a mixture thereof.

Next, Step 2 is described.

In the Step 2, the compound (M-22a), the compound (M-22b) or the mixturethereof is reacted with an oxidizing agent to give Present compound(Ik).

The reaction is usually carried out in a solvent. Examples of thesolvent to be used in the reaction include ethers, aliphatichydrocarbons, aromatic hydrocarbons, halogenated aliphatic hydrocarbons,nitriles, polar aprotic solvent, nitrogen-containing aromatic compounds,and mixed solvents thereof.

Examples of the oxidizing agent to be used in the reaction includemanganese dioxide.

Instead of using the oxidizing agent, the compound (M-22a), the compound(M-22b) or the mixture thereof may be reacted with methanesulfonylchloride and triethylamine successively, or the mixture ofmethanesulfonyl chloride and triethylamine.

Instead of using the oxidizing agent, the compound (M-22a), the compound(M-22b) or the mixture thereof may be reacted with Pd—C and olefins suchas vinyl acetate successively, or the mixture of Pd—C and vinyl acetate.

In the reaction, the oxidizing agent is usually used within a range of 1to 10 molar ratio(s) as opposed to 1 mole of the compound (M-22a) or thecompound (M-22b).

In the reaction, when methanesulfonyl chloride and triethylamine areused instead of the oxidizing agent, the methanesulfonyl chloride isusually used within a range of 1 to 10 molar ratio(s), and thetriethylamine is usually used within a range of 1 to 10 molar ratio(s),as opposed to 1 mole of the compound (M-22a) or the compound (M-22b).

In the reaction, when Pd—C and olefins such as vinyl acetate are usedinstead of the oxidizing agent, the Pd—C is usually used within a rangeof 0.001 to 1 molar ratio(s), and the olefins is usually used within arange of 1 to 10 molar ratio(s), as opposed to 1 mole of the compound(M-22a) or the compound (M-22b).

The reaction temperature is usually within a range of 0 to 200° C. Thereaction period of the reaction is usually within a range of 0.1 to 24hours.

When the reaction is completed, to the reaction mixtures is added water,and the reaction mixtures are then extracted with organic solvents, andthe organic layers are worked up (for example, drying and concentration)to isolate the Present compound (Ik).

Process 9

A compound represented by formula (Ii) (hereinafter, referred to asPresent compound (Ii)) may be prepared according to a method describedbelow.

[wherein the symbols are the same as defined above.]

First, the process for preparing the compound represented by formula(M-21) (hereinafter, referred to as Compound (M-21)) from the compound(M-20) is described.

The compound (M-21) may be prepared by reacting the compound (M-20) witha compound represented by formula (R-6) (hereinafter, referred to asCompound (R-6)).

The reaction is usually carried out in a solvent. Examples of thesolvent to be used in the reaction include ethers, aliphatichydrocarbons, aromatic hydrocarbons, halogenated aliphatic hydrocarbons,nitriles, polar aprotic solvent, nitrogen-containing aromatic compounds,and mixed solvents thereof.

In the reaction, the compound (R-6) is usually used within a range of 1to 10 molar ratio(s) as opposed to 1 mole of the compound (M-20).

The reaction temperature is usually within a range of 0 to 200° C. Thereaction period of the reaction is usually within a range of 0.1 to 24hours.

When the reaction is completed, to the reaction mixtures is added water,and the resulting mixtures are then extracted with organic solvents, andthe organic layers are worked up (for example, drying and concentration)to isolate the compound (M-21).

Next, the process for preparing the Present compound (Ii) from thecompound (M-21) is described.

The Present compound (Ii) may be prepared by reacting the compound(M-21) with a halogenating agent.

The reaction is usually carried out in a solvent. Examples of thesolvent to be used in the reaction include ethers, aliphatichydrocarbons, aromatic hydrocarbons, halogenated aliphatic hydrocarbons,nitriles, polar aprotic solvent, nitrogen-containing aromatic compounds,and mixed solvents thereof.

Examples of the halogenating agent to be used in the reaction includeN-bromosuccinimide, N-chlorosuccinimide, sulfuryl chloride, and bromine.

A catalyst may be added to the reaction as needed. Examples of thecatalyst to be used in the reaction include benzoyl peroxide.

In the reaction, a halogenating agent is usually used within a range of1 to 10 molar ratio(s), and the catalyst is usually used within a rangeof 0.1 to 0.5 molar ratio(s), as opposed to 1 mole of the compound(M-21).

The reaction temperature is usually within a range of 0 to 200° C. Thereaction period of the reaction is usually within a range of 0.1 to 24hours.

When the reaction is completed, to the reaction mixtures is added water,and the resulting mixtures are then extracted with organic solvents, andthe organic layers are worked up (for example, drying and concentration)to isolate the Present compound (Ii).

Process 10

A compound represented by formula (Ij) (hereinafter, referred to asPresent compound (Ij)) may be prepared by reacting the compound (M-20)with a compound represented by formula (R-8) (hereinafter, referred toas Compound (R-8)).

[wherein, the symbols are the same as defined above.]

The reaction is usually carried out in a solvent. Examples of thesolvent to be used in the reaction include ethers, aliphatichydrocarbons, aromatic hydrocarbons, halogenated aliphatic hydrocarbons,nitriles, alcohols, polar aprotic solvent, nitrogen-containing aromaticcompounds, and mixed solvents thereof.

In the reaction, the compound (R-8) is usually used within a range of 1to 10 molar ratio(s) as opposed to 1 mole of the compound (M-20)).

The reaction temperature is usually within a range of 0 to 200° C. Thereaction period of the reaction is usually within a range of 0.1 to 24hours.

When the reaction is completed, to the reaction mixtures is added water,and the resulting mixtures are then extracted with organic solvents, andthe organic layers are worked up (for example, drying and concentration)to isolate the Present compound (Ij).

Process 11

A compound represented by formula (Ik) (hereinafter, referred to asPresent compound (Ik)) may be prepared according to a method describedbelow.

[wherein, the symbols are the same as defined above.]

First, Step 1 is explained.

In the Step 1, a compound represented by formula (M-7) (hereinafter,referred to as Compound (M-7)) and a compound represented by formula(R-5) (hereinafter, referred to as Compound (R-5)) are reacted to give acompound represented by formula (M-23) (hereinafter, referred to asCompound (M-23)).

The reaction is usually carried out in a solvent. Examples of thesolvent to be used in the reaction include ethers, aliphatichydrocarbons, aromatic hydrocarbons, halogenated aliphatic hydrocarbons,alcohols, esters, nitriles, polar aprotic solvent, nitrogen-containingaromatic compounds, and mixed solvents thereof.

In the reaction, the compound (R-5) is usually used within a range of 1to 10 molar ratio(s) as opposed to 1 mole of the compound (M-7)).

The reaction temperature is usually within a range of 0 to 200° C. Thereaction period of the reaction is usually within a range of 0.1 to 24hours.

When the reaction is completed, the reaction mixtures are worked up (forexample, drying and concentration) to isolate the compound (M-23).Alternatively, when the reaction is completed, the resulting compound(M-23) is not isolated and is used as itself in Step 2, or the reactionmixtures are concentrated to obtain the residues, which are used asitself in the Step 2.

Next, Step 2 is described.

In the Step 2, the compound (M-23) is reacted with ammonia to give thecompound (M-22a) and the compound (M-22b).

The reaction is usually carried out in a solvent. Examples of thesolvent to be used in the reaction include ethers, aliphatichydrocarbons, aromatic hydrocarbons, halogenated aliphatic hydrocarbons,alcohols, esters, nitriles, polar aprotic solvent, nitrogen-containingaromatic compounds, and mixed solvents thereof.

Examples of the ammonia to be used in the reaction include aqueousammonia solution and solution of ammonia in methanol.

The ammonia to be used in the reaction may be in the form of a gas, ormay be in the form of an aqueous solution or an alcoholic solution.Alternatively, ammonium carboxylate such as ammonium acetate; ammoniumphosphate such as ammonium dihydrogenphosphate; ammonium carbonate;

ammonium halides such as ammonium chloride may be used.

In the reaction, ammonia is usually used within a range of 1 to 10 molarratio(s) as opposed to 1 mole of the compound (M-7).

The reaction temperature is usually within a range of 0 to 200° C. Thereaction period of the reaction is usually within a range of 0.1 to 24hours.

When the reaction is completed, to the reaction mixtures is added water,and the reaction mixtures are then extracted with organic solvents, andthe organic layers are worked up (for example, drying and concentration)to give the compound (M-22a), the compound (M-22b) or the mixturethereof. Alternatively, when the reaction is completed, the resultingcompound (M-22a), the resulting compound (M-22b) or the resultingmixture thereof is not isolated and is used as itself in Step 3, or thereaction mixtures are concentrated to obtain the residues, which areused as itself in the Step 3.

Next, Step 3 is described.

In the Step 3, the compound (M-22a), the compound (M-22b), or themixture thereof may be reacted with an oxidizing agent according to themethod described in the Step 2 of the Process 8 to prepare the Presentcompound (Ik).

Hereinafter, a process for preparing each intermediate compound isdescribed.

Reference Process 1

The compound (M-1) may be prepared by reacting a compound represented byformula (M-8) (hereinafter, referred to Compound (M-8)) with a compoundrepresented by formula (M-9) (hereinafter, referred to Compound (M-9))in the presence of a metal catalyst.

[wherein V³ represents a chlorine atom, a bromine atom or an iodineatom; M represents 9-borabicyclo[3.3.1]nona-9-yl group, —B(OH)₂,4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl group, Sn(n-C₄H₉)₃, ZnCl,MgI, or MgBr; and the other symbols are the same as defined above.]

The compound (M-9) may be prepared according to a similar method to thatdescribed in International Publication 03/024961 or Organic ProcessResearch & Development, 2004, 8, 192-200.

The compound (M-8) may be prepared according to a similar method to thatdescribed in International Publication 2010/016005.

The reaction is usually carried out in a solvent. Examples of thesolvent to be used in the reaction include ethers, aromatichydrocarbons, polar aprotic solvent, water, and mixed solvents thereof.

Examples of the metal catalyst to be used in the reaction includepalladium catalysts such as tetrakis(triphenylphosphine)palladium(0),1,1′-bis(diphenylphosphino)ferrocene palladium(II) dichloride,tris(dibenzylideneacetone)dipalladium(0), and palladium(II) acetate;nickel catalysts such as bis(cyclooctadiene)nickel(0) and nickel(II)chloride; and copper catalyst such as copper(I) iodide and copper(I)chloride.

A ligand, a base and/or an inorganic halogenated compound may be addedto the reaction as needed.

Examples of the ligand to be used in the reaction includetriphenylphosphine, Xantphos,2,2′-bis(diphenylphoshino)-1,1′-binaphthyl,1,1′-bis(diphenylphoshino)ferrocene,2-(dicyclohexylphosphino)-2′,4′,6′-triisopropyl-1,1′-biphenyl,2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl,1,2-bis(diphenylphosphino)ethane, 2,2′-bipyridine, 2-aminoethanol,8-hydroquinoline, and 1,10-phenanthroline.

Examples of the base to be used in the reaction include alkali metalhydrides, alkali metal carbonates, and organic bases.

Examples of the inorganic halogenated compounds include alkali metalfluorides such as potassium fluoride, and sodium fluoride; and alkalimetal chlorides such as lithium chloride, and sodium chloride.

In the reaction, the compound (M-9) is usually used within a range of 1to 10 molar ratio(s), the metal catalyst is usually used within a rangeof 0.01 to 0.5 molar ratios, the ligand is usually used within a rangeof 0.01 to 1 molar ratio(s), the base is usually used within a range of0.1 to 5 molar ratios, and the inorganic halogenated compound is usuallyused within a range of 0.1 to 5 molar ratios, as opposed to 1 mole ofthe compound (M-8).

The reaction temperature is usually within a range of −20 to 200° C. Thereaction period of the reaction is usually within a range of 0.1 to 24hours.

When the reaction is completed, to the reaction mixtures is added water,and the reaction mixtures are then extracted with organic solvent(s),and the organic solvents are worked up (for example, drying andconcentration) to give the compound (M-1).

Reference Process 2

The compound (M-3) may be prepared by reacting a compound represented byformula (M-11) (hereinafter, referred to as Compound (M-11)) with anacid.

[wherein, RX represents a methyl group or an ethyl group; and the othersymbols are the same as defined above.]

The reaction is usually carried out in a solvent. Examples of a solventto be used in the reaction include halogenated aliphatic hydrocarbons,aromatic hydrocarbons, nitriles, alcohols, acetic acid, water, and mixedsolvents thereof.

Examples of the acid to be used in the reaction include mineral acidssuch as hydrochloric acid; boron halides such as boron trichloride andboron tribromide; metal chlorides such as titanium chloride, andaluminium chloride.

In the reaction, the acid is usually used within a range of 0.1 to 10molar ratio(s) as opposed to 1 mole of the compound (M-11). In thereaction, when the mineral acids are used as an acid, the mineral acidmay be used also as a solvent.

The reaction temperature is usually within a range of −20 to 150° C. Thereaction period of the reaction is usually within a range of 0.1 to 24hours.

When the reaction is completed, to the reaction mixtures is added water,and the reaction mixtures are then extracted with organic solvents, andthe organic layers are worked up (for example, drying and concentration)to give the compound (M-3).

Reference Process 3

The compound (M-11) wherein n is 0 (hereinafter, referred to as Compound(M-11a)), the compound (M-11) wherein n is 1 (hereinafter, referred toas Compound (M-11b)), and the compound (M-11) wherein n is 2(hereinafter, referred to as Compound (M-11c)) may be prepared accordingto a method described below.

[wherein the symbols are the same as defined above.]

A compound represented by formula (M-13) (hereinafter, referred to asCompound (M-13)) may be prepared by using a compound represented byformula (M-12) (hereinafter, referred to as Compound (M-12)) instead ofthe compound (M-8) according to the similar method to that described inReference Process 1.

The compound (M-12) is a commercially available compound, or may beprepared according to the similar method to a well-known method.

The compound (M-11a) may be prepared by using the compound (M-13)instead of the compound (M-1) according to a method described in Process3.

The compound (M-11b) and the compound (M-11c) may be prepared by usingthe compound (M-11a) instead of the compound (Ia) according to thesimilar method to that described in Process 1.

Reference Process 4

A compound represented by formula (M-17) (hereinafter, referred to asCompound (M-17)) may be prepared by reacting a compound represented byformula (M-16) (hereinafter, referred to as Compound (M-16)) with thecompound (R-12), followed by reacting the reaction mixtures withammonia.

[wherein R³⁸ represents a halogen atom, or a C1-C4 alkoxy group, and thesymbols are the same as defined above.]

The reaction may be carried out by using the compound (M-16) instead ofthe compound (M-7) according to the similar method to that described inProcess 5.

Reference Process 5

The compound (M-16) may be prepared by reacting a compound representedby formula (M-15) (hereinafter, referred to as Compound (M-15)) with acompound represented by formula (R-16) (hereinafter, referred to asCompound (R-16)) in the presence of a base.

[wherein R^(y) represents a methyl group, or an ethyl group, and theother symbols are the same as defined above.]

The compound (M-15) is a commercially available compound, or may beprepared according to the similar method to that described inInternational Publication No. 2014/204730.

The compound (R-16) is a commercially available compound, or may beprepared according to the method described in Journal of MolecularCatalysis A: Chemical, 2011, 341 (1-2), 57-62.

The reaction is usually carried out in a solvent. Examples of thesolvent to be used in the reaction include alcohols, ethers, aromatichydrocarbons, polar aprotic solvents, and mixed solvents thereof.

Examples of the base to be used in the reaction include n-butyl lithium,s-butyl lithium, t-butyl lithium, lithium diisopropylamide, sodiumbis(trimethylsilyl)amide, potassium bis(trimethylsilyl)amide, potassiumt-butoxide, sodium methoxide, sodium ethoxide, and alkali metalhydrides.

In the reaction, the compound (R-16) is usually used within a range of 1to 5 molar ratio(s), and the base is usually used within a range of 1 to5 molar ratio(s), as opposed to 1 mole of the compound (M-15).Preferably, the compound (R-16) is usually used within a range of 1 to1.1 molar ratio(s), and the base is usually used within a range of 1 to2 molar ratio(s), as opposed to 1 mole of the compound (M-15).

The reaction temperature is usually within a range of −78 to 100° C. Thereaction period of the reaction is usually within a range of 0.5 to 12hours.

When the reaction is completed, to the reaction mixtures is added water,and the reaction mixtures are then extracted with organic solvents, andthe organic layers are worked up (for example, drying and concentration)to give the compound (M-16).

The compound (M-15) and the compound (M-16) are commercially availablecompounds or may be prepared by known methods.

Reference Process 6

A compound represented by formula (M-4a) (hereinafter, referred to asCompound (M-4a)) and a compound represented by formula (M-4b)(hereinafter, referred to as Compound (M-4b) may be prepared accordingto a method described below.

[wherein, V⁴ represents a chlorine atom or a bromine atom, V⁵ representsa fluorine atom or an iodine atom, and the other symbols are the same asdefined above]

First, a method for preparing the compound (M-4a) from the compound(M-3) is described.

The compound (M-4a) may be prepared by reacting the compound (M-3) withphosphoryl chloride or phosphoryl bromide.

The reaction is usually carried out in a solvent. Examples of thesolvent to be used in the reaction include aromatic hydrocarbons.

When phosphoryl chloride is used, phosphoryl chloride may be used alsoas a solvent.

In the reaction, phosphoryl chloride or phosphoryl bromide is usuallyused within a range of 1 to 10 molar ratio(s) as opposed to 1 mole ofthe compound (M-3).

The reaction temperature is usually within a range of 0 to 150° C. Thereaction period of the reaction is usually within a range of 0.5 to 24hours.

When the reaction is completed, to the reaction mixtures is added water,and the reaction mixtures are then extracted with organic solvents, andthe organic layers are worked up (for example, drying and concentration)to give the compound (M-4a).

Next, a method for preparing the compound (M-4b) from the compound(M-4a) is described.

The compound (4-b) may be prepared by reacting the compound (M-4a) witha inorganic fluoride compound or an inorganic iodide compound.

The reaction is usually carried out in a solvent. Examples of thesolvents to be used in the reaction include nitriles, polar aproticsolvent, nitrogen-containing aromatic compounds, and mixed solventsthereof.

Examples of the inorganic fluoride compound to be used in the reactioninclude potassium fluoride, sodium fluoride and cesium fluoride.

Examples of the inorganic iodide compound to be used in the reactioninclude potassium iodide and sodium iodide.

When the compound (M-4b) wherein V⁵ represents a fluorine atom isprepared, the inorganic fluoride compound is usually used within a rangeof 1 to 10 molar ratio(s) as opposed to 1 mole of the compound (M-4a).

When the compound (M-4b) wherein V⁵ represents an iodine atom isprepared, the inorganic iodide compound is usually within a range of 1to 10 molar ratio(s) as opposed to 1 mole of the compound (M-4a).

The reaction temperature is usually within a range of 0 to 250° C. Thereaction period of the reaction is usually within a range of 0.5 to 24hours.

When the reaction is completed, to the reaction mixtures is added water,and the reaction mixtures are then extracted with organic solvents, andthe organic layers are worked up (for example, drying and concentration)to give the compound (M-4b).

Reference Process 7

A compound represented by formula (M-19) (hereinafter, referred to asCompound (M-19)) may be prepared according to a method described below.

[wherein the symbols are the same as defined above.]

The reaction may be prepared by using a compound represented by formula(M-14) (hereinafter, referred to as Compound (M-14)) instead of thecompound (M-20) according to the similar method to that described inProcess 8.

Reference Process 8

The compound (M-19) may be prepared according to a method describedbelow.

[wherein the symbols are the same as defined above.]

The reaction may be prepared by using a compound represented by formula(M-16) (hereinafter, referred to as Compound (M-16)) instead of thecompound (M-7) according to the similar method to that described inProcess 11.

Reference Process 9

A compound represented by formula (M-28) (hereinafter, referred to asCompound (M-28)) may be prepared by reacting a compound represented byformula (M-16) (hereinafter, referred to as Compound (M-16)) with thecompound (R-12), followed by reacting the reaction mixtures withammonia.

[wherein the symbols are the same as defined above.]

The reaction may be prepared by using the compound (M-16) instead of thecompound (M-7) according to the similar method to that described inProcess 5.

Reference Process 10

A compound represented by formula (M-29) (hereinafter, referred to asCompound (M-29)) may be prepared by reacting the compound (M-14) withthe compound (R-8).

[wherein the symbols are the same as defined above.]

The reaction may be prepared by using the compound (M-14) instead of thecompound (M-20) according to the similar method to that described inProcess 10.

Reference Process 11

The compound (M-31) may be prepared by reacting the compound (M-30) withammonia.

[wherein the symbols are the same as defined above.]

The reaction is usually carried out in a solvent. Examples of thesolvent to be used in the reaction include ethers, aromatichydrocarbons, nitriles, alcohols, polar aprotic solvents, water, andmixed solvents thereof.

The ammonia to be used in the reaction may be in the form of a gas, ormay be in the form of an aqueous solution or an alcoholic solution.Alternatively, ammonium carboxylate such as ammonium acetate; ammoniumphosphate such as ammonium dihydrogenphosphate; ammonium carbonate;ammonium halides such as ammonium chloride may be used.

In the reaction, the ammonia is usually used within a range of 0.1 to100 molar ratio(s) as opposed to 1 mole of the compound (M-30).

The reaction temperature is usually within a range of 0 to 200° C. Thereaction period of the reaction is usually within a range of 0.5 to 24hours.

When the reaction is completed, to the reaction mixtures is added water,and the reaction mixtures are then extracted with organic solvents, andthe organic layers are worked up (for example, drying and concentration)to give the compound (M-31).

Reference Process 12

The compound (M-2) may be prepared by reacting the compound (M-1) with asulfating agent.

[wherein the symbols are the same as defined above.]

The reaction is usually carried out in a solvent. Examples of thesolvents to be used in the reaction include ethers, aromatichydrocarbons, nitriles, polar aprotic solvent, and mixed solventsthereof.

Examples of the sulfating agent to be used in the reaction includesodium sulfide and sodium hydrogen sulfide.

In the reaction, the sulfating agent is usually used within a range of 1to 10 molar ratio(s) as opposed to 1 mole of the compound (M-1).

The reaction temperature is usually within a range of −20 to 150° C. Thereaction period of the reaction is usually within a range of 0.5 to 24hours.

When the reaction is completed, to the reaction mixtures is added water,and the reaction mixtures are then extracted with organic solvents, andthe organic layers are worked up (for example, drying and concentration)to give the compound (M-2).

In the reaction, V is preferably a fluorine atom or a chlorine atom.

Examples of the compound (M-1) include the following compounds.

The compound (M-1) wherein R¹ represents a C2-C10 haloalkyl group, or a(C1-C5 alkoxy)C2-C5 alkyl group having one or more halogen atoms; and R³represents independently of each other a C1-C6 chain hydrocarbon groupoptionally having one or more substituents selected from Group B, aphenyl group optionally having one or more substituents selected fromGroup D, a 5 or 6 membered aromatic heterocyclic group optionally havingone or more substituents selected from Group D, a OR¹², a NR¹¹R¹², aNR²⁹NR¹¹R¹², or a halogen atom.

The compound (M-1) wherein R¹ represents a C2-C10 haloalkyl group, or a(C1-C5 alkoxy)C2-C5 alkyl group having one or more halogen atoms; and R³represents independently of each other a C1-C6 chain hydrocarbon groupoptionally having one or more substituents selected from Group B, aphenyl group optionally having one or more substituents selected fromGroup D, a 6 membered aromatic heterocyclic group having one to twonitrogen atoms (the 6 membered aromatic heterocyclic group mayoptionally have one or more substituents selected from Group D), a 5membered aromatic heterocyclic group having one to four nitrogen atoms(the 5 membered aromatic heterocyclic group may optionally have one ormore substituents selected from Group D), a OR¹², a NR¹¹R¹², aNR²⁹NR¹¹R¹², or a halogen atom.

The compound (M-1) wherein A¹ represents a nitrogen atom or a CH; V²represents a fluorine atom, or a chlorine atom; R¹ represents a C2-C10haloalkyl group, or a (C1-C5 alkoxy)C2-C5 alkyl group having one or morehalogen atoms; R³ represents independently of each other a C1-C6 chainhydrocarbon group optionally having one or more halogen atoms, or ahalogen atom; and R⁶ represents independently of each other a C1-C6alkyl group optionally having one or halogen atoms, or a halogen atom.

The compound (M-1) wherein A¹ represents a nitrogen atom or a CH; V²represents a fluorine atom, or a chlorine atom; R¹ represents a C2-C10haloalkyl group having two or more fluorine atoms; R³ representsindependently of each other a C1-C6 chain hydrocarbon group optionallyhaving one or more halogen atoms, or a halogen atom; and p represents 0.

The compound (M-1) wherein A¹ represents a nitrogen atom or a CH; V²represents a fluorine atom, or a chlorine atom; R¹ represents a C2-C10haloalkyl group having two or more fluorine atoms; R³ representsindependently of each other a C1-C6 chain hydrocarbon group optionallyhaving one or more halogen atoms, or a halogen atom; and p represents 0.

The compound (M-1) wherein A¹ represents a nitrogen atom or a CH; V²represents a fluorine atom, or a chlorine atom; R¹ represents a2,2,2-trifluoroethyl group, a 2,2,3,3-tetrafluoropropyl group, a2,2,3,3,3-pentafluoropropyl group, a 1,1,2,3,3,3-hexafluoropropyl group,a 1,1,2-trifluoro-2-(trifluoromethoxy)ethyl group, or a2,2,3,4,4,4-hexafluorobutyl group; q represents 0 or 1; R³ represents atrifluoromethyl group; and p represents 0.

Examples of the compound (M-2) include the following compounds.

The compound (M-2) wherein R¹ represents a C2-C10 haloalkyl group, or a(C1-C5 alkoxy)C2-C5 alkyl group having one or more halogen atom; and R³represents independently of each other a C1-C6 chain hydrocarbon groupoptionally having one or more halogen atoms, a phenyl group optionallyhaving one or more substituents selected from Group D, a 5 or 6 memberedaromatic heterocyclic group optionally having one or more substituentsselected from Group D, a OR¹², a NR¹¹R¹², a NR²⁹NR¹¹R¹², or a halogenatom.

The compound (M-2) wherein R¹ represents a C2-C10 haloalkyl group, or a(C1-C5 alkoxy)C2-C5 alkyl group having one or more halogen atom; and R³represents independently of each other a C1-C6 chain hydrocarbon groupoptionally having one or more halogen atoms, a phenyl group optionallyhaving one or more substituents selected from Group D, a 6 memberedaromatic heterocyclic group having one to two nitrogen atoms (the 6membered aromatic heterocyclic group may optionally have one or moresubstituents selected from Group D), a 5 membered aromatic heterocyclicgroup having one to four nitrogen atoms (the 5 membered aromaticheterocyclic group may optionally have one or more substituents selectedfrom Group D), a OR¹², a NR¹¹R¹², a NR²⁹NR¹¹R¹², or a halogen atom.

The compound (M-2) wherein A¹ represents a nitrogen atom or a CH; R¹represents a C2-C10 haloalkyl group or a (C1-C5 alkoxy)C2-C5 alkyl grouphaving one or more halogen atom; R³ represents independently of eachother a C1-C6 chain hydrocarbon group optionally having one or morehalogen atoms, or a halogen atom; and R⁶ represents independently ofeach other a C1-C6 alkyl group optionally having one or halogen atoms ora halogen atom.

The compound (M-2) wherein A¹ represents a nitrogen atom or a CH; R¹represents a C2-C10 alkyl group having two or more fluorine atoms; R³represents independently of each other a C1-C6 chain hydrocarbon groupoptionally having one or more halogen atoms, or a halogen atom; and prepresents 0.

The compound (M-2) wherein A¹ represents a nitrogen atom or a CH; R¹represents a C2-C10 alkyl group; q represents 0; and p represents 0.

The compound (M-2) wherein A¹ represents a nitrogen atom or a CH; R¹represents a C2-C10 haloalkyl group having two or more fluorine atoms;R³ represents independently of each other a C1-C6 chain hydrocarbongroup optionally having one or more halogen atoms, or a halogen atom;and p represents 0.

The compound (M-2) wherein A¹ represents a nitrogen atom or a CH; R¹represents a 2,2,2-trifluoroethyl group, a 2,2,3,3-tetrafluoropropylgroup, a 2,2,3,3,3-pentafluoropropyl group, a1,1,2,3,3,3-hexafluoropropyl group, a1,1,2-trifluoro-2-(trifluoromethoxy)ethyl group, or a2,2,3,4,4,4-hexafluorobutyl group; q represents 0 or 1; R³ represents atrifluoromethyl group; and p represents 0.

Examples of the compound (M-3) include the following compounds.

The compound (M-3) wherein R² represents a C1-C6 alkyl group optionallyhaving one or halogen atoms; and R³ represents independently of eachother a C1-C6 chain hydrocarbon group optionally having one or morehalogen atoms, a phenyl group optionally having one or more substituentsselected from Group D, a 5 or 6 membered aromatic heterocyclic groupoptionally having one or more substituents selected from Group D, aOR¹², a NR¹¹R¹², a NR²⁹NR¹¹R¹², or a halogen atom.

The compound (M-3) wherein R² represents a C1-C6 alkyl group optionallyhaving one or halogen atoms; and R³ represents independently of eachother a C1-C6 chain hydrocarbon group optionally having one or morehalogen atoms, a phenyl group optionally having one or more substituentsselected from Group D, a 6 membered aromatic heterocyclic group havingone to two nitrogen atoms (the 6 membered aromatic heterocyclic groupmay optionally have one or more substituents selected from Group D), a 5membered aromatic heterocyclic group having one to four nitrogen atoms(the 5 membered aromatic heterocyclic group may optionally have one ormore substituents selected from Group D), a OR¹², a NR¹¹R¹², or ahalogen atom.

The compound (M-3) wherein A¹ represents a nitrogen atom, or a CH; R²represents an ethyl group; q represents 0, 1, 2, or 3; R³ representsindependently of each other a C1-C6 chain hydrocarbon group optionallyhaving one or more halogen atoms, a 5 or 6 membered aromaticheterocyclic group optionally having one or more substituents selectedfrom Group D, a OR¹², a NR¹¹R¹², a NR²⁹NR¹¹R¹², or a halogen atom; andR⁶ represents independently of each other a C1-C6 alkyl group optionallyhaving one or halogen atoms, or a halogen atom.

The compound (M-3) wherein A¹ represents a nitrogen atom, or a CH; R²represents an ethyl group; q represents 0, 1, 2, or 3; R³ representsindependently of each other a C1-C6 chain hydrocarbon group optionallyhaving one or more halogen atoms, or a halogen atom; p represents 0, 1,2, or 3; and R⁶ represents independently of each other a C1-C6 alkylgroup optionally having one or halogen atoms or a halogen atom.

Examples of the compound (M-4) include the following compounds.

The compound (M-4) wherein R² represents a C1-C6 alkyl group optionallyhaving one or halogen atoms; and R³ represents independently of eachother a C1-C6 chain hydrocarbon group optionally having one or morehalogen atoms, a phenyl group optionally having one or more substituentsselected from Group D, a 5 or 6 membered aromatic heterocyclic groupoptionally having one or more substituents selected from Group D, aOR¹², a NR¹¹R¹², a NR²⁹NR¹¹R¹², or a halogen atom.

The compound (M-4) wherein R² represents a C1-C6 alkyl group optionallyhaving one or halogen atoms; and R³ represents independently of eachother a C1-C6 chain hydrocarbon group optionally having one or morehalogen atoms, a phenyl group optionally having one or more substituentsselected from Group D, a 6 membered aromatic heterocyclic group havingone to two nitrogen atoms (the 6 membered aromatic heterocyclic groupmay optionally have one or more substituents selected from Group D), a 5membered aromatic heterocyclic group having one to four nitrogen atoms(the 5 membered aromatic heterocyclic group may optionally have one ormore substituents selected from Group D), a OR¹², a NR¹¹R¹², or ahalogen atom.

The compound (M-4) wherein A¹ represents a nitrogen atom, or a CH; Vrepresents a fluorine atom, a chlorine atom, or an iodine atom; R²represents an ethyl group; R³ represents independently of each other aC1-C6 chain hydrocarbon group optionally having one or more halogenatoms, or a halogen atom; and R⁶ represents independently of each othera C1-C6 alkyl group optionally having one or halogen atoms, or a halogenatom.

Examples of the compound (M-30) include the following compounds.

The compound (M-30) wherein R¹ represents a C2-C10 haloalkyl group, or a(C1-C5 alkoxy)C2-C5 alkyl group having one or more halogen atom; and R²represents a C1-C6 alkyl group optionally having one or halogen atoms.

The compound (M-30) wherein R⁴⁰ represents a halogen atom, or a OR¹; R¹represents a C2-C10 haloalkyl group, or a (C1-C5 alkoxy)C2-C5 alkylgroup having one or more halogen atom; and R² represents a C1-C6 alkylgroup optionally having one or halogen atoms.

The compound (M-30) wherein R⁴⁰ represents a halogen atom, or a OR¹; R¹represents a C2-C10 haloalkyl group; and R² represents an ethyl group.

The compound (M-30) wherein R⁴⁰ represents a halogen atom, or a OR¹; R¹represents a C2-C10 haloalkyl group; R² represents an ethyl group; and prepresents 0.

The compound (M-30) wherein R⁴⁰ represents a halogen atom; and R²represents a C1-C6 alkyl group optionally having one or halogen atoms.

The compound (M-30) wherein R⁴⁰ represents a fluorine atom or a chlorineatom; and R² represents an ethyl group; n represents 2; and p represents0.

The compound (M-23) wherein R⁴⁰ represents a OR⁴; R⁴ represents a C2-C10haloalkyl group or a (C1-C5 alkoxy)C2-alkyl group having one or morehalogen atom; and R² represents an ethyl group.

The compound (M-23) wherein R⁴⁰ represents a OR⁴; R⁴ represents a C2-C10haloalkyl group having two or more fluorine atoms or a (C1-C5alkoxy)C2-C5 alkyl group having one or more halogen atom; R² representsan ethyl group; n represents 2; and p represents 0.

The compound (M-30) wherein R⁴⁰ represents a OR¹; R¹ represents a2,2,2-trifluoroethyl group, a 2,2,3,3-tetrafluoropropyl group, a2,2,3,3,3-pentafluoropropyl group, a 1,1,2,3,3,3-hexafluoropropyl group,a 1,1,2-trifluoro-2-(trifluoromethoxy)ethyl group, or a2,2,3,4,4,4-hexafluorobutyl group; R² represents an ethyl group; nrepresents 2; and p represents 0.

The compound (M-30) wherein R⁴⁰ represents a C1-C4 alkoxy group; R²represents an ethyl group; p represents 0, 1, 2, or 3; and R⁶ representsindependently of each other a C1-C6 alkyl group optionally having one orhalogen atoms, a NR¹⁸R¹⁹, a C(O)OR²⁵, a OC(O)OR²⁰, a cyano group, anitro group, or a halogen atom.

The compound (M-30) wherein R⁴⁰ represents a C1-C3 alkoxy group; R²represents an ethyl group; n represents 2; and p represents 0.

Examples of the compound (M-31) include the following compounds.

The compound (M-31) wherein R¹ represents a C2-C10 haloalkyl group, or a(C1-C5 alkoxy)C2-C5 alkyl group having one or more halogen atom; and R²represents a C1-C6 alkyl group optionally having one or halogen atoms.

The compound (M-31) wherein R⁴⁰ represents a halogen atom; and R²represents a C1-C6 alkyl group optionally having one or halogen atoms;

The compound (M-31) wherein R⁴⁰ represents a fluorine atom or a chlorineatom; R² represents an ethyl group; n represents 2; and p represents 0.

The compound (M-31) wherein R⁴⁰ represents a OR¹; R¹ represents a C2-C10haloalkyl group, or a (C1-C5 alkoxy)C2-C5 alkyl group having one or morehalogen atom; and R² represents an ethyl group.

The compound (M-31) wherein R⁴⁰ represents a OR¹; R¹ represents a C2-C10haloalkyl group having two or more fluorine atoms, or a (C1-C5alkoxy)C2-C5 alkyl group having one or more halogen atom; R² representsan ethyl group; n represents 2; and p represents 0.

The compound (M-31) wherein R⁴⁰ represents a OR¹; R¹ represents a2,2,2-trifluoroethyl group, a 2,2,3,3-tetrafluoropropyl group, a2,2,3,3,3-pentafluoropropyl group, a 1,1,2,3,3,3-hexafluoropropyl group,a 1,1,2-trifluoro-2-(trifluoromethoxy)ethyl group, or a2,2,3,4,4,4-hexafluorobutyl group; R² represents an ethyl group; nrepresents 2; and p represents 0.

The compound (M-31) wherein R⁴⁰ represents a C1-C4 alkoxy group; and R²represents an ethyl group.

The compound (M-31) wherein R⁴⁰ represents a C1-C3 alkoxy group; R²represents an ethyl group; n represents 2; and p represents 0.

Next, specific examples of the compound of the present invention areshown below.

The compound represented by formula (I-C) of the present inventionwherein n represents 2; R^(3a), R^(3b), R^(3c), R^(6a), and R^(6b)represent a hydrogen atom; and R⁴ and R² represent any combinationindicated in Table 1 to Table 5 (hereinafter, referred to as CompoundGroup SX1).

TABLE 1 R¹ R² CF₂HCH₂ CH₃CH₂ CH₃CF₂ CH₃CH₂ CF₃CH₂ CH₃CH₂ CCl₃CH₂ CH₃CH₂CF₂HCF₂ CH₃CH₂ CHClFCF₂ CH₃CH₂ CF₃CH₂CH₂ CH₃CH₂ CF₂HCF₂CH₂ CH₃CH₂CF₃CF₂CH₂ CH₃CH₂ CBrF₂CF₂ CH₃CH₂ CF₃CFHCF₂ CH₃CH₂ CH₃CF₂CH₂ CH₃CH₂CF₃CH(CH₃) CH₃CH₂ CF₃C(CH₃)₂ CH₃CH₂ CH(CH₃)₂CH(CF₃) CH₃CH₂ (CF₃)₂CHCH₃CH₂ CH₃CH₂CH(CF₃) CH₃CH₂ CF₃CCl₂CH₂ CH₃CH₂ CF₃CF₂CH(CH₃) CH₃CH₂CF₃CF₂CH(CH₂CH₃) CH₃CH₂ C(CH₃)(CF₃)₂CH₂ CH₃CH₂ CF₃CFHCF₂CH₂ CH₃CH₂CF₃(CF₂)₂CH₂ CH₃CH₂ CBrF₂CF₂CH₂CH₂ CH₃CH₂ CF₃CFHCF₂CH(CH₃) CH₃CH₂

TABLE 2 R¹ R² CF₃CH═CHCH₂ CH₃CH₂ CF₃(CF₂)₃CH₂ CH₃CH₂ CF₃(CF₂)₄CH₂ CH₃CH₂CF₃(CF₂)₃CH₂CH₂ CH₃CH₂ CF(CF₃)₂CF₂CF₂CH₂CH₂ CH₃CH₂ CF₂H(CF₂)₃CH₂ CH₃CH₂CF₂H(CF₂)₅CH₂ CH₃CH₂ CF₃(CF₂)₃CH₂CH₂CH₂ CH₃CH₂ CF₃CF₂(CH₂)₅CH₂ CH₃CH₂CF₃(CF₂)₅CH₂CH₂CH₂ CH₃CH₂ CF₃(CF₂)₃CH₂(CH₂)₄CH₂ CH₃CH₂ CF₃(CF₂)₅CH₂CH₂CH₃CH₂ CF(CF₃)₂CH₂(CH₂)₄CH₂ CH₃CH₂ CF₃OCFHCF₂ CH₃CH₂ CH₃OCH₂CF₂CH₂CH₃CH₂ CF₃CH₂OCH₂CF₂CH₂ CH₃CH₂ CH₂FCF₂CH₂ CH₃CH₂ CH₂ClCF₂CH₂ CH₃CH₂CH₂BrCF₂CH₂ CH₃CH₂ CH₃OCH₂(CF₂)CH₂ CH₃CH₂ CF₃CH₂OCH₂(CF₂)₂CH₂ CH₃CH₂CH₂F(CF₂)₂CH₂ CH₃CH₂ CH₂Cl(CF₂)₂CH₂ CH₃CH₂ CH₂Br(CF₂)₂CH₂ CH₃CH₂CH₃OCH₂(CF₂)₃CH₂ CH₃CH₂

TABLE 3 R¹ R² CF₃CH₂OCH₂(CF₂)₃CH₂ CH₃CH₂ CH₃OCH₂(CF₂)₃CH₂ CH₃CH₂CF₃CH₂OCH₂(CF₂)₃CH₂ CH₃CH₂ CH₂F(CF₂)₃CH₂ CH₃CH₂ CH₂Cl(CF₂)₃CH₂ CH₃CH₂CH₂Br(CF₂)₃CH₂ CH₃CH₂ CH₃OCH₂(CF₂)₄CH₂ CH₃CH₂ CF₃CH₂OCH₂(CF₂)₄CH₂ CH₃CH₂CH₂F(CF₂)₄CH₂ CH₃CH₂ CH₂Cl(CF₂)₄CH₂ CH₃CH₂ CH₂Br(CF₂)₄CH₂ CH₃CH₂CF₃CF₂OCFHCF₂ CH₃CH₂ CF₃CF₂CF₂OCFHCF₂ CH₃CH₂ CF₃CF₂CF₂OCF(CF₃)CH₂ CH₃CH₂CF₃CH₂OCH₂CH₂ CH₃CH₂

TABLE 4 R¹ R²

CH₃CH₂

CH₃CH₂

CH₃CH₂

CH₃CH₂

CH₃CH₂

CH₃CH₂

CH₃CH₂

TABLE 5 R² R² CH₃SCH₂CF₂CH₂ CH₃CH₂ CH₃S(O)CH₂CF₂CH₂ CH₃CH₂CH₃S(O)₂CH₂CF₂CH₂ CH₃CH₂ CF₃CH₂SCH₂CF₂CH₂ CH₃CH₂ CF₃CH₂S(O)CH₂CF₂CH₂CH₃CH₂ CF₃CH₂S(O)CH₂CF₂CH₂ CH₃CH₂ CF₃SCH₂CF₂CH₂ CH₃CH₂ CF₃S(O)CH₂CF₂CH₂CH₃CH₂ CF₃S(O)₂CH₂CF₂CH₂ CH₃CH₂ CF₃SCH₂(CF₂)₂CH₂ CH₃CH₂CF₃S(O)CH₂(CF₂)₂CH₂ CH₃CH₂ CF₃S(O)₂CH₂(CF₂)₂CH₂ CH₃CH₂ CF₃SCH₂(CF₂)₃CH₂CH₃CH₂ CF₃S(O)CH₂(CF₂)₃CH₂ CH₃CH₂ CF₃S(O)₂CH₂(CF₂)₃CH₂ CH₃CH₂CF₃SCH₂(CF₂)₄CH₂ CH₃CH₂ CF₃S(O)CH₂(CF₂)₄CH₂ CH₃CH₂ CF₃S(O)₂CH₂(CF₂)₄CH₂CH₃CH₂ CF₃CH₂SCH₂CH₂ CH₃CH₂ CF₃CH₂S(O)CH₂CH₂ CH₃CH₂ CF₃CH₂S(O)₂CH₂CH₂CH₃CH₂ CF₃SCH₂CH₂ CH₃CH₂ CF₃S(O)CH₂CH₂ CH₃CH₂ CF₃S(O)₂CH₂CH₂ CH₃CH₂

The compound represented by formula (I-C) of the present inventionwherein n represents 1; R^(3a), R^(3b), R^(3c), R^(6a), and R^(6b)represent a hydrogen atom; and R¹ and R² represent any combinationindicated in Table 1 to Table 5 (hereinafter, referred to as CompoundGroup SX2).

The compound represented by formula (I-C) of the present inventionwherein n represents 0; R^(3a), R^(3b), R^(3c), R^(6a), and R^(6b)represent a hydrogen atom; and R¹ and R² represent any combinationindicated in Table 1 to Table 5 (hereinafter, referred to as CompoundGroup SX3).

The compound represented by formula (I-C) of the present inventionwherein n represents 2; R^(3a), R^(3c), R^(6a), and R^(6b) represent ahydrogen atom; R^(3b) represents a trifluoromethyl group; and R¹ and R²represent any combination indicated in Table 1 to Table 5 (hereinafter,referred to as Compound Group SX4).

The compound represented by formula (I-C) of the present inventionwherein n represents 1; R^(3a), R^(3c), R^(6a), and R^(6b) represent ahydrogen atom; R^(3b) represents a trifluoromethyl group; and R¹ and R²represent any combination indicated in Table 1 to Table 5 (hereinafter,referred to as Compound Group SX5).

The compound represented by formula (I-C) of the present inventionwherein n represents 0; R^(3a), R^(3c), R^(6a), and R^(6b) represent ahydrogen atom; R^(3b) represents a trifluoromethyl group; and R¹ and R²represent any combination indicated in Table 1 to Table 5 (hereinafter,referred to as Compound Group SX6).

The compound represented by formula (I-D) of the present inventionwherein R⁴ represents a hydrogen atom; n represents 2; R^(3a), R^(3b),R^(3c), R^(6a), and R^(6b) represent a hydrogen atom; and R¹ and R²represent any combination indicated in Table 1 to Table 5 (hereinafter,referred to as Compound Group SX7).

The compound represented by formula (I-D) of the present inventionwherein R⁴ represents a hydrogen atom; n represents 1; R^(3a), R^(3b),R^(3c), R^(6a), and R^(6b) represent a hydrogen atom; and R¹ and R²represent any combination indicated in Table 1 to Table 5 (hereinafter,referred to as Compound Group SX8).

The compound represented by formula (I-D) of the present inventionwherein R⁴ represents a hydrogen atom; n represents 0; R^(3a), R^(3b),R^(3c), R^(6a), and R^(6b) represent a hydrogen atom; and R¹ and R²represent any combination indicated in Table 1 to Table 5 (hereinafter,referred to as Compound Group SX9).

The compound represented by formula (I-D) of the present inventionwherein R⁴ represents a hydrogen atom; n represents 2; R^(3a), R^(3c),R^(6a), and R^(6b) represent a hydrogen atom; R^(3b) represents atrifluoromethyl group; and R¹ and R² represent any combination indicatedin Table 1 to Table 5 (hereinafter, referred to as Compound Group SX10).

The compound represented by formula (I-D) of the present inventionwherein R⁴ represents a hydrogen atom; n represents 1; R^(3a), R^(3c),R^(6a), and R^(6b) represent a hydrogen atom; R^(3b) represents atrifluoromethyl group; and R¹ and R² represent any combination indicatedin Table 1 to Table 5 (hereinafter, referred to as Compound Group SX11).

The compound represented by formula (I-D) of the present inventionwherein R⁴ represents a hydrogen atom; n represents 0; R^(3a), R^(3c),R^(6a), and R^(6b) represent a hydrogen atom; R^(3b) represents atrifluoromethyl group; and R¹ and R² represent any combination indicatedin Table 1 to Table 5 (hereinafter, referred to as Compound Group SX12).

The compound represented by formula (I-D) of the present inventionwherein R⁴ represents a fluorine atom; n represents 2; R^(3a), R^(3b),R^(3c), R^(6a), and R^(6b) represent a hydrogen atom; and R¹ and R²represent any combination indicated in Table 1 to Table 5 (hereinafter,referred to as Compound Group SX13).

The compound represented by formula (I-D) of the present inventionwherein R⁴ represents a fluorine atom; n represents 1; R^(3a), R^(3b),R^(3c), R^(6a), and R^(6b) represent a hydrogen atom; and R¹ and R²represent any combination indicated in Table 1 to Table 5 (hereinafter,referred to as Compound Group SX14).

The compound represented by formula (I-D) of the present inventionwherein R⁴ represents a fluorine atom; n represents 0; R^(3a), R^(3b),R^(3c), R^(6a), and R^(6b) represent a hydrogen atom; and R¹ and R²represent any combination indicated in Table 1 to Table 5 (hereinafter,referred to as Compound Group SX15).

The compound represented by formula (I-D) of the present inventionwherein R⁴ represents a fluorine atom; n represents 0; R^(3a), R^(3c),R^(6a), and R^(6b) represent a hydrogen atom; R^(3b) represents atrifluoromethyl group; and R¹ and R² represent any combination indicatedin Table 1 to Table 5 (hereinafter, referred to as Compound Group SX16).

The compound represented by formula (I-D) of the present inventionwherein R⁴ represents a fluorine atom; n represents 1; R^(3a), R^(3c),R^(6a), and R^(6b) represent a hydrogen atom; R^(3b) represents atrifluoromethyl group; and R¹ and R² represent any combination indicatedin Table 1 to Table 5 (hereinafter, referred to as Compound Group SX17).

The compound represented by formula (I-D) of the present inventionwherein R⁴ represents a fluorine atom; n represents 0; R^(3a), R^(3c),R^(6a), and R^(6b) represent a hydrogen atom; R^(3b) represents atrifluoromethyl group; and R¹ and R² represent any combination indicatedin Table 1 to Table 5 (hereinafter, referred to as Compound Group SX18).

The compound of the present invention may be mixed or combined with oneor more kinds of ingredients selected from a group consisting of thefollowing Group (a), Group (b), Group (c), and Group (d) (hereinafter,referred to as Present active ingredient). Preferably, the presentactive ingredient includes one or more kinds of ingredients selectedfrom a group consisting of sub group a-1, sub group a-2, sub group a-3,sub group a-4, sub group a-5, sub group a-6, sub group a-7, sub groupa-8, sub group a-9, sub group b-1, sub group b-2, sub group b-3, subgroup b-4, sub group b-5, sub group b-6, sub group b-7, sub group b-8,sub group b-9, sub group b-10, sub group b-11, sub group b-12, sub groupb-13, sub group b-14, sub group b-15, sub group b-16, sub group c-1, subgroup c-2, and Group (d). Particularly preferably, the present activeingredient includes one or more kinds of ingredients selected from agroup consisting of sub group a-6, sub group a-9, sub group b-1, subgroup b-3, sub group b-4, sub group b-5, sub group b-9, sub group b-11,and sub group b-13.

Group (a) represents a group of one or more kinds of insecticidalingredients, miticidal ingredients, and nematicidal ingredients selectedfrom the group consisting of the following sub group a-1 to a-10. Thenumerical number in bracket represents a CAS register number.

Sub Group a-1:

Carbamate acetylcholinesterase (AChE) inhibitor group selected from thegroup consisting of alanycarb, aldicarb, bendiocarb, benfuracarb,butocarboxim, butoxycarboxim, carbaryl: NAC, carbofuran, carbosulfan,ethiofencarb, fenobucarb: BPMC, formetanate, furathiocarb, isoprocarb:MIPC, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur:PHC, thiodicarb, thiofanox, triazamate, trimethacarb, XMC, andxylylcarb.Sub Group a-2:Organophosphorus acetylcholinesterase (AChE) inhibitor group selectedfrom the group consisting of acephate, azamethiphos, azinphos-ethyl,azinphos-methyl, cadusafos, chlorethoxyfos, chlorfenvinphos,chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos:CYAP, demeton-S-methyl, diazinon, dichlorvos: DDVP, dicrotophos,dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos,famphur, fenamiphos, fenitrothion: MEP, fenthion: MPP, fosthiazate,heptenophos, imicyafos, isofenphos,isopropyl-O-(methoxyaminothiophosphoryl)salicylate, isoxathion,malathion, mecarbam, methamidophos, methidathion: DMTP, mevinphos,monocrotophos, naled: BRP, omethoate, oxydemeton-methyl, parathion,parathion-methyl, phenthoate: PAP, phorate, phosalone, phosmet: PMP,phosphamidon, phoxim, pirimiphos-methyl, profenofos, propetamphos,prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep,tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon,triazophos, trichlorfon: DEP, and vamidothion.Sub Group a-3:GABA-gated chloride channel blockers group selected from the groupconsisting of ethiprole, fipronil, flufiprole, chlordane, endosulfan,and alpha-endosulfan.Sub Group a-4:GABA-gated chloride channel allosteric modulator group selected from thegroup consisting of afoxolaner, fluralaner, broflanilide, andfluxametamide.Sub Group a-5:Sodium channel modulator group selected from the group consisting ofacrinathrin, allethrin, bifenthrin, kappa-bifenthrin, bioallethrin,bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin,gamma-cyhalothrin, lambda-cyhalothrin, cypermethrin, alpha-cypermethrin,beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin,deltamethrin, empenthrin, esfenvalerate, etofenprox, fenpropathrin,fenvalerate, flucythrinate, flumethrin, fluvalinate, tau-fluvalinate,halfenprox, heptafluthrin, imiprothrin, kadethrin, meperfluthrin,momfluorothrin, permethrin, phenothrin, prallethrin, pyrethrins,resmethrin, silafluofen, tefluthrin, kappa-tefluthrin, tetramethrin,tetramethylfluthrin, tralomethrin, transfluthrin, benfluthrin,flufenoprox, flumethrin, sigma-cypermethrin, furamethrin, metofluthrin,profluthrin, dimefluthrin, epsilon-metofluthrin, epsilon-momfluorothrin,and methoxychlor.Sub Group a-6:Nicotinic acetylcholine receptor (nAChR) competitive modulator groupselected from the group consisting of acetamiprid, clothianidin,dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam,sulfoxaflor, flupyradifurone, triflumezopyrim, dicloromezotiaz,cycloxaprid, and a compound represented by the following formula:

(1363400-41-2, hereinafter, referred to as insecticidal compound α1).Sub Group a-7:Ryanodine receptor modulator group selected from the group consisting ofchlorantraniliprole, cyantraniliprole, cycloniliprole, flubendiamide,tetraniliprole, cyhalodiamide, and a compound represented by thefollowing formula:

(1104384-14-6, hereinafter, referred to as insecticidal compound α2).Sub Group a-8:Microbial material group selected from the group consisting of Beauveriabassiana, Beauveria bassiana strain GHA, Beauveria brongniartii,Paecilomyces fumosoroseus, Paecilomyces lilacinus, Paecilomycestenuipes, Verticillium lecani, Arthrobotrys dactyloides, Bacillusthuringiensis, Bacillus firmus, Bacillus firmus strain CNCM 1-1582,Bacillus megaterium, Hirsutella rhossiliensis, Hirsutella minnesotensis,Monacrosporium phymatopagus, Pasteuria nishizawae, Pasteuria penetrans,Pasteuria usgae, and Verticillium chlamydosporium.Sub Group a-9:Nematicidal ingredients group selected from the group consisting ofabamectin, fluazaindolizine, fluensulfone, fluopyram, and tioxazafen.Sub Group a-10:The other group as insecticides and miticides selected from the groupconsisting of spinetoram, spinosad, emamectin-benzoate, lepimectin,milbemectin, hydroprene, kinoprene, methoprene, fenoxycarb,pyriproxyfen, methyl bromide, chloropicrin, sulfuryl fluoride, sodiumaluminium fluoride or chiolite, borax, boric acid, disodium octaborate,sodium borate, sodium metaborate, tartar emetic, dazomet, metam,pymetrozine, pyrifluquinazone, clofentezine, hexythiazox, diflovidazin,etoxazole, diafenthiuron, azocyclotin, cyhexatin, fenbutatin oxide,propargite, tetradifon, chlorfenapyr, DNOC, sulfluramid, bensultap,cartap, cartap hydrochloride, thiocyclam, thiosultap-disodium,thiosultap-monosodium, bistrifluron, chlorfluazuron, diflubenzuron,fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron,novaluron, noviflumuron, teflubenzuron, triflumuron, buprofezin,cyromazine, chromafenozide, halofenozide, methoxyfenozide, tebufenozide,amitraz, hydramethylnon, acequinocyl, fluacrypyrim, bifenazate,fenazaquin, fenpyroximate, pyridaben, pyrimidifen, tebufenpyrad,tolfenpyrad, rotenone, indoxacarb, metaflumizone, spirodiclofen,spiromesifen, spirotetramat, aluminium phosphide, calcium phosphide,phosphine, zinc phosphide, calcium cyanide, potassium cyanide, sodiumcyanide, cyenopyrafen, cyflumetofen, pyflubumide, flonicamid,azadirachtin, benzoximate, bromopropylate, chinomethionat, dicofol,pyridalyl, lime sulfur, sulfur, machine oil, nicotine, nicotine-sulfate,afidopyropen, flometoquin, metoxadiazone, pyriminostrobin, a compoundrepresented by the following formula:

(1477919-27-9, hereinafter, referred to as fungicide compound α3),a compound represented by the following formula:

(1477923-37-7, hereinafter, referred to as fungicide compound α4), anda compound represented by the following formula:

(1449021-97-9, hereinafter, referred to as fungicide compound α5).

Group (b) represents a fungicidal ingredient group selected from thegroup consisting of the following sub group b-1 to sub group b-18.

Sub Group b-1

PA fungicide (Phenyl amide) selected from the group consisting ofbenalaxyl, benalaxyl-M, furalaxyl, metalaxyl, metalaxyl-M, oxadixyl, andofurace.

Sub Group b-2

MBC fungicide (methyl benzimidazole carbamate) group selected from thegroup consisting of benomyl, carbendazim, fuberidazole, thiabendazole,thiophanate, and thiophanate-methyl.

Sub Group b-3

Thiazole carboxamide group selected from the group consisting ofethaboxam.

Sub Group b-4

SDHI (Succinate dehydrogenase inhibitor) group selected from the groupconsisting of benodanil, flutolanil, mepronil, isofetamid, fenfuram,carboxin, oxycarboxin, thifluzamide, benzovindiflupyr, bixafen,fluxapyroxad, furametpyr, isopyrazam, penflufen, penthiopyrad, sedaxane,pydiflumetofen, boscalid, pyraziflumid,3-difluoromethyl-1-methyl-N-(1,1,3-trimethylindan)-4-yl)pyrazole-4-carboxamide(141573-94-6, hereinafter, referred to as fungicide compound β1),3-difluoromethyl-1-methyl-N-[(3R)-1,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide(1352994-67-2, hereinafter, referred to as fungicide compound β2),3-difluoromethyl-N-(7-fluoro-1,1,3-trimethylindan-4-yl)-1-methylpyrazole-4-carboxamide(1383809-87-7, hereinafter, referred to as fungicide compound β3),3-difluoromethyl-N-[(3R)-7-fluoro-1,1,3-trimethylindan-4-yl)-1-methylpyrazole-4-carboxamide(1513466-73-3, hereinafter, referred to as fungicide compound β4), andN-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(5-chloro-2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide(1255734-28-1, hereinafter, referred to as fungicide compound β5).Sub Group b-5QoI fungicide (Qo Inhibitor) group selected from the group consisting ofazoxystrobin, coumoxystrobin, enoxastrobin, flufenoxystrobin,picoxystrobin, pyraoxystrobin, mandestrobin, pyraclostrobin,pyrametostrobin, triclopyricarb, kresoxim-methyl, trifloxystrobin,dimoxystrobin, fenaminstrobin, metominostrobin, orysastrobin,famoxadone, fluoxastrobin, fenamidone, and pyribencarb.Sub Group b-6QiI fungicide (Qi Inhibitor) group selected from the group consisting ofcyazofamid, amisulbrom, binapacryl, meptyldinocap, dinocap, andfluazinam.Sub Group b-7Thiophanate carboxamide group selected from the group consisting ofsilthiofam.Sub Group b-8AP fungicide (Anilinopyrimidine) group selected from the groupconsisting of cyprodinil, mepanipyrim, and pyrimethanil.Sub Group b-9PP fungicide (Phenylpyrrole) group selected from the group consisting offenpiclonil and fludioxonil.Sub Group b-10AH fungicide (Aromaic hydrocarbons) group selected from the groupconsisting of biphenyl, chloroneb, dicloran, quintozene, tecnazene, andtolclofos-methyl.Sub Group b-11DMI fungicide (Demethylation inhibitor) group selected from the groupconsisting of azaconazole, bitertanol, bromuconazole, cyproconazole,difenoconazole, diniconazole, diniconazole-M, fenbuconazole,fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole,ipconazole, ipfentrifluconazole, mefentrifluconazole, metconazole,myclobutanil, penconazole, propiconazole, simeconazole, tebuconazole,tetraconazole, triadimefon, triadimenol, triticonazole, prothioconazole,triforine, pyrifenox, pyrisoxazole, fenarimol, nuarimol, imazalil,oxpoconazole, oxpoconazole fumarate, pefurazoate, prochloraz, andtriflumizole.Sub Group b-12CCA fungicide (Carboxylic acid amide) group selected from the groupconsisting of dimethomorph, flumorph, pyrimorph, benthiavalicarb,benthivalicarb-isopropyl, iprovalicarb, valifenalate, and mandipropamid.Sub Group b-13Piperidinyl thiazole isoxazoline group selected from the groupconsisting of oxathiapiprolin.Sub Group b-14Tetrazolyl oxime group selected from the group consisting ofpicarbutrazox.Sub Group b-15Dithiocarbamate group selected from the group consisting of ferbam,mancozeb, maneb, metiram, propineb, thiram, zineb, and ziram.Sub Group b-16Phthalimide group selected from the group consisting of captan,captafol, and folpet.Sub Group b-17Microbial fungicide group selected from the group consisting ofAgrobacterium radiobactor, Bacillus amyloliquefaciens, Bacillusamyloliquefaciens strain QST713, Bacillus amyloliquefaciens strainFZB24, Bacillus amyloliquefaciens strain MBI600, Bacillusamyloliquefaciens strain D747, Bacillus amyloliquefaciens strain AT-332,Bacillus pumilus, Bacillus pumilus strain GB34, Bacillus pumilus strainQST2808, Bacillus subtilis, Erwinia carotovora (CGE234M403 strain and soon), Pseudomonas fluorescens (G7090 strain and so on), Talaromycesflavus (SAY-Y-94-01 strain and so on), Trichoderma atroviride (SKT-1strain and so on), Trichoderma harzianum, and Harpin protein.Sub Group b-18Other fungicide group selected from the group consisting of bupirimate,dimethirimol, ethirimol, hymexazole, octhilinone, oxolinic acid,diethofencarb, zoxamide, pencycuron, fluopicolide, phenamacril,diflumetorim, tolfenpyrad, fentin acetate, fentin chloride, fentinhydroxide, ametoctradin, blasticidin-S, kasugamycin, streptomycin,oxytetracycline, quinoxyfen, proquinazid, chlozolinate, dimethachlone,iprodione, procymidone, vinclozolin, edifenphos, iprobenfos, pyrazophos,isoprothiolane, etridiazole, iodocarb, propamocarb, prothiocarb,aldimorph, dodemorph, fenpropidin, fenpropimorph, piperalin,spiroxamine, tridemorph, fenhexamid, fenpyrazamine, pyributicarb,naftifine, terbinafine, polyoxins, phthalide, pyroquilon, tricyclazole,carpropamid, diclocymet, fenoxanil, tolprocarb, acibenzolar-S-methyl,probenazole, tiadinil, isotianil, laminarin, cymoxanil, fosetyl,teclofthalam, triazoxide, flusulfamide, diclomezine, methasulfocarb,cyflufenamid, metrafenone, pyriofenone, dodine, flutianil, ferimzone,tebufloquin, validamycin, basic copper chloride, copper(II) hydroxide,basic copper sulfate, Dodecylbenzenesulphonic acid bisethylenediaminecopper [II] salt (DBEDC)), organocopper, sulfur, chlorothalonil,dichlofluanid, tolylfluanid, guazatine, iminoctadine, anilazine,dithianon, chinomethionat, fluoroimide, dipymetitrone, quinofumelin,dichlobentiazox,3-chloro-5-phenyl-6-methyl-4-(2,6-difluorophenyl)pyridadine(1358061-55-8; hereinafter, referred to as fungicide compound β6),a compound represented by the following formula:

(517875-34-2; hereinafter, referred to as fungicide compound β7),N′-[4-({3-[(4-chlorophenyl)methyl]-1,2,4-thiadiazol-5-yl}oxy)-2,5-dimethylphenyl]-N-ethyl-N-methylmethaneimidamide(1202781-91-6; hereinafter, referred to as fungicide compound β8),4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine(1362477-26-6; hereinafter, referred to as fungicide compound β9),2,2-dimethy-9-fluoro-5-(quinolin-3-yl)-2,3-dihydrobenzo[f][1,4]oxazepine(1207749-50-5; hereinafter, referred to as fungicide compound β10),2-[6-(3-fluoro-4-methoxyphenyl)-4-methylpyridin-2-yl]quinazoline(1257056-97-5; hereinafter, referred to as fungicide compound β11),5-fluoro-2-[(4-methylphenyl)methoxy]-4-pyrimidineamine (1174376-25-0;hereinafter, referred to as fungicide compound β12),5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidine-2(1H)-one(1616664-98-2; hereinafter, referred to as fungicide compound β13),N′-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylmethaneimideamide(1052688-31-9; hereinafter, referred to as fungicide compound β14),N′-{4-[(4,5-dichlorothiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylmethaneimideamide(929908-57-6; hereinafter, referred to as fungicide compound β15), ethyl(2Z)-3-amino-2-cyano-3-phenylacrylate (39491-78-6; hereinafter, referredto as fungicide compound β16),N-[(2-chlorothiazol-5-yl)methyl]-N-ethyl-6-methoxy-3-nitropyridine-2-amine(1446247-98-8; hereinafter, referred to as fungicide compound β17), and1-[2-({[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}methyl)-3-methylpenyl]-4-methyl-5-oxo-4,5-dihydro-1H-tetrazole(1472649-01-6, hereinafter, referred to as fungicide compound β18).

Group (c) represents a plant growth modulating ingredients groupselected from the group consisting of the following sub group c-1, subgroup c-2, and sub group c-3.

Sub Group c-1:

Plant growth modulating ingredients group selected from the groupconsisting of ethephon, chlormequat, chlormequat-chloride, mepiquat,mepiquat-chloride, Gibberellin A3, abscisic acid, Kinetin,benzyladenine, forchlorfenuron, and thidiazuron.

Sub Group c-2:

Mycorrhizal fungi group selected from the group consisting of Glomusspp., Glomus intraradices, Glomus mosseae, Glomus aggregatum, and Glomusetunicatum.

Sub Group c-3:

Root nodule bacteria group selected from the group consisting ofBradyrhizobium elkani, Bradyrhizobium japonicum, Bradyrhizobium lupini,Rhizobium leguminosarum bv. trifolii, Rhizobium leguminosarum bv.phaseoli, Rhizobium leguminosarum bv. viciae, Sinorhizobium meliloti,and Rhizobium spp.Group (d):Phytotoxicity-reducing ingredient group selected from the groupconsisting of benoxacor, cloquintocet-mexyl, cyometrinil, dichlormid,fenchlorazole-ethyl, fenclorim, flurazole, furilazole, mefenpyr-diethyl,MG191 (2-(dichloromethyl)-2-methyl-1,3-dioxolane), oxabetrinil,allidochlor, isoxadifen-ethyl, cyprosulfamide, fluxofenim,1,8-naphthalic anhydride, and AD-67 (4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5] decane).

Examples of the combination of the present active ingresient and thePresent compound in the present composition are described below. Thesymbol of “SX” represents any one of the Present compound selected fromthe compound group SX1 to the compound group SX18. Also, all thebelow-mentioned present active ingredient are known active ingredients,and are commercially available, may be produced by the known method, orare available from the bacterial authority depository.

alanycarb+SX, aldicarb+SX, bendiocarb+SXbenfuracarb+SX, butocarboxim+SX,butoxycarboxim+SX, carbaryl: NAC+SX, carbofuran+SX, carbosulfan+SX,ethiofencarb+SX, fenobucarb: BPMC+SX, formetanate+SX, furathiocarb+SX,isoprocarb: MIPC+SX, methiocarb+SX, methomyl+SX, metolcarb+SX,oxamyl+SX, pirimicarb+SX, propoxur: PHC+SX, thiodicarb+SX, thiofanox+SX,triazamate+SX, trimethacarb+SX, XMC+SX, xylylcarb+SX;

acephate+SX, azamethiphos+SX, azinphos-ethyl+SX, azinphos-methyl+SX,cadusafos+SX, chlorethoxyfos+SX, chlorfenvinphos+SX, chlormephos+SX,chlorpyrifos+SX, chlorpyrifos-methyl+SX, coumaphos+SX, cyanophos:CYAP+SX, demeton-S-methyl+SX, diazinon+SX, dichlorvos: DDVP+SX,dicrotophos+SX, dimethoate+SX, dimethylvinphos+SX, disulfoton+SX,EPN+SX, ethion+SX, ethoprophos+SX, famphur+SX, fenamiphos+SX,fenitrothion: MEP+SX, fenthion: MPP+SX, fosthiazate+SX, heptenophos+SX,imicyafos+SX, isofenphos+SX,isopropyl-O-(methoxyaminothiophosphoryl)salicylate+SX, isoxathion+SX,malathion+SX, mecarbam+SX, methamidophos+SX, methidathion: DMTP+SX,mevinphos+SX, monocrotophos+SX, naled: BRP+SX, omethoate+SX,oxydemeton-methyl+SX, parathion+SX, parathion-methyl+SX, phenthoate:PAP+SX, phorate+SX, phosalone+SX, phosmet: PMP+SX, phosphamidon+SX,phoxim+SX, pirimiphos-methyl+SX, profenofos+SX, propetamphos+SX,prothiofos+SX, pyraclofos+SX, pyridaphenthion+SX, quinalphos+SX,sulfotep+SX, tebupirimfos+SX, temephos+SX, terbufos+SX,tetrachlorvinphos+SX, thiometon+SX, triazophos+SX, trichlorfon: DEP+SX,vamidothion+SX;

ethiprole+SX, fipronil+SX, flufiprole+SX, chlordane+SX, endosulfan+SX,alpha-endosulfan+SX;

afoxolaner+SX, fluralaner+SX, broflanilide+SX, fluxametamide+SX;

acrinathrin+SX, allethrin+SX, bifenthrin+SX, kappa-bifenthrin+SX,bioallethrin+SX, bioresmethrin+SX, cycloprothrin+SX, cyfluthrin+SX,beta-cyfluthrin+SX, cyhalothrin+SX, gamma-cyhalothrin+SX,lambda-cyhalothrin+SX, cypermethrin+SX, alpha-cypermethrin+SX,beta-cypermethrin+SX, theta-cypermethrin+SX, zeta-cypermethrin+SX,cyphenothrin+SX, deltamethrin+SX, empenthrin+SX, esfenvalerate+SX,etofenprox+SX, fenpropathrin+SX, fenvalerate+SX, flucythrinate+SX,flumethrin+SX, fluvalinate+SX, tau-fluvalinate+SX, halfenprox+SX,heptafluthrin+SX, imiprothrin+SX, kadethrin+SX, meperfluthrin+SX,momfluorothrin+SX, permethrin+SX, phenothrin+SX, prallethrin+SX,pyrethrins+SX, resmethrin+SX, silafluofen+SX, tefluthrin+SX,kappa-tefluthrin+SX, tetramethrin+SX, tetramethylfluthrin+SX,tralomethrin+SX, transfluthrin+SX, benfluthrin+SX, flufenoprox+SX,flumethrin+SX, sigma-cypermethrin+SX, furamethrin+SX, metofluthrin+SX,profluthrin+SX, dimefluthrin+SX, epsilon-metofluthrin+SX,epsilon-momfluorothrin+SX, methoxychlor+SX;acetamiprid+SX, clothianidin+SX, dinotefuran+SX, imidacloprid+SX,nitenpyram+SX, thiacloprid+SX, thiamethoxam+SX, sulfoxaflor+SX,flupyradifurone+SX, triflumezopyrim+SX, dicloromezotiaz+SX,cycloxaprid+SX, insecticidal compound α1+SX;chlorantraniliprole SX, cyantraniliprole SX, cycloniliprole+SX,flubendiamide+SX, tetraniliprole+SX, cyhalodiamide+SX, insecticidalcompound α2+SX;Beauveria bassiana+SX, Beauveria bassiana strain GHA+SX, Beauveriabrongniartii+SX, Paecilomyces fumosoroseus+SX, Paecilomyceslilacinus+SX, Paecilomyces tenuipes+SX, Verticillium lecani+SX,Arthrobotrys dactyloides+SX, Bacillus thuringiensis+SX, Bacillusfirmus+SX, Bacillus firmus strain CNCM 1-1582+SX, Bacillusmegaterium+SX, Hirsutella rhossiliensis+SX, Hirsutella minnesotensis+SX,Monacrosporium phymatopagus+SX, Pasteuria nishizawae+SX, Pasteuriapenetrans+SX, Pasteuria usgae+SX, Verticillium chlamydosporium+SX;abamectin+SX, fluazaindolizine+SX, fluensulfone+SX, fluopyram+SX,tioxazafen+SX;spinetoram+SX, spinosad+SX, emamectin-benzoate+SX, lepimectin+SX,milbemectin+SX, hydroprene+SX, kinoprene+SX, methoprene+SX,fenoxycarb+SX, pyriproxyfen+SX, methyl bromide+SX, chloropicrin+SX,sulfuryl fluoride+SX, sodium aluminium fluoride or chiolite+SX,borax+SX, boric acid+SX, disodium octaborate+SX, sodium borate+SX,sodium metaborate+SX, tartar emetic+SX, dazomet+SX, metam+SX,pymetrozine+SX, pyrifluquinazone+SX, clofentezine+SX, hexythiazox+SX,diflovidazin+SX, etoxazole+SX, diafenthiuron+SX, azocyclotin+SX,cyhexatin+SX, fenbutatin oxide+SX, propargite+SX, tetradifon+SX,chlorfenapyr+SX, DNOC+SX, sulfluramid+SX, bensultap+SX, cartap+SX,cartap hydrochloride+SX, thiocyclam+SX, thiosultap-disodium+SX,thiosultap-monosodium+SX, bistrifluron+SX, chlorfluazuron+SX,diflubenzuron+SX, fluazuron+SX, flucycloxuron+SX, flufenoxuron+SX,hexaflumuron+SX, lufenuron+SX, novaluron+SX, noviflumuron+SX,teflubenzuron+SX, triflumuron+SX, buprofezin+SX, cyromazine+SX,chromafenozide+SX, halofenozide+SX, methoxyfenozide+SX, tebufenozide+SX,amitraz+SX, hydramethylnon+SX, acequinocyl+SX, fluacrypyrim+SX,bifenazate+SX, fenazaquin+SX, fenpyroximate+SX, pyridaben+SX,pyrimidifen+SX, tebufenpyrad+SX, tolfenpyrad+SX, rotenone+SX,indoxacarb+SX, metaflumizone+SX, spirodiclofen+SX, spiromesifen+SX,spirotetramat+SX, aluminium phosphide+SX, calcium phosphide+SX,phosphine+SX, zinc phosphide+SX, calcium cyanide+SX, potassiumcyanide+SX, sodium cyanide+SX, cyenopyrafen+SX, cyflumetofen+SX,pyflubumide+SX, flonicamid+SX, azadirachtin+SX, benzoximate+SX,bromopropylate+SX, chinomethionat+SX, dicofol+SX, pyridalyl+SX, limesulfur+SX, sulfur+SX, machine oil+SX, nicotine+SX, nicotine-sulfate+SX,afidopyropen+SX, flometoquin+SX, metoxadiazone+SX, pyriminostrobin+SX,insecticidal compound α3+SX, insecticidal compound α4+SX, insecticidalcompound α5+SX;benalaxyl+SX, benalaxyl-M+SX, furalaxyl+SX, metalaxyl+SX,metalaxyl-M+SX, oxadixyl+SX, ofurace+SX;benomyl+SX, carbendazim+SX, fuberidazole+SX, thiabendazole+SX,thiophanate+SX, thiophanate-methyl+SX;ethaboxam+SX;benodanil+SX, flutolanil+SX, mepronil+SX, isofetamid+SX, fenfuram+SX,carboxin+SX, oxycarboxin+SX, thifluzamide+SX, benzovindiflupyr+SX,bixafen+SX, fluxapyroxad+SX, furametpyr+SX, isopyrazam+SX, penflufen+SX,penthiopyrad+SX, sedaxane+SX, pydiflumetofen+SX, boscalid+SX,pyraziflumid+SX, fungicide compound β1+SX, fungicide compound β2+SX,fungicide compound β3+SX, fungicide compound β4+SX, fungicide compoundβ5+SX;azoxystrobin+SX, coumoxystrobin+SX, enoxastrobin+SX,flufenoxystrobin+SX, picoxystrobin+SX, pyraoxystrobin+SX,mandestrobin+SX, pyraclostrobin+SX, pyrametostrobin+SX,triclopyricarb+SX, kresoxim-methyl+SX, trifloxystrobin+SX,dimoxystrobin+SX, fenaminstrobin+SX, metominostrobin+SX,orysastrobin+SX, famoxadone+SX, fluoxastrobin+SX, fenamidone+SX,pyribencarb+SX;cyazofamid+SX, amisulbrom+SX, binapacryl+SX, meptyldinocap+SX,dinocap+SX, fluazinam+SX;silthiofam+SX;cyprodinil+SX, mepanipyrim+SX, pyrimethanil+SX;fenpiclonil+SX, fludioxonil+SX;biphenyl+SX, chloroneb+SX, dicloran+SX, quintozene+SX, tecnazene+SX,tolclofos-methyl+SX;azaconazole+SX, bitertanol+SX, bromuconazole+SX, cyproconazole+SX,difenoconazole+SX, diniconazole+SX, diniconazole-M+SX, epoxiconazole+SX,etaconazole+SX, fenbuconazole+SX, fluquinconazole+SX, flusilazole+SX,flutriafol+SX, hexaconazole+SX, imibenconazole+SX, ipconazole+SX,ipfentrifluconazole+SX, mefentrifluconazole+SX, metconazole+SX,myclobutanil+SX, penconazole+SX, propiconazole+SX, simeconazole+SX,tebuconazole+SX, tetraconazole+SX, triadimefon+SX, triadimenol+SX,triticonazole+SX, prothioconazole+SX, triforine+SX, pyrifenox+SX,pyrisoxazole+SX, fenarimol+SX, nuarimol+SX, imazalil+SX,oxpoconazole+SX, oxpoconazole fumarate+SX, pefurazoate+SX,prochloraz+SX, triflumizole+SX;dimethomorph+SX, flumorph+SX, pyrimorph+SX, benthiavalicarb+SX,benthivalicarb-isopropyl+SX, iprovalicarb+SX, valifenalate+SX,mandipropamid+SX;oxathiapiprolin+SX;picarbutrazox+SX;ferbam+SX, mancozeb+SX, maneb+SX, metiram+SX, propineb+SX, thiram+SX,zineb+SX, ziram+SX;captan+SX, captafol+SX, folpet+SX;Agrobacterium radiobactor+SX, Bacillus amyloliquefaciens+SX, Bacillusamyloliquefaciens strain QST713+SX, Bacillus amyloliquefaciens strainFZB24+SX, Bacillus amyloliquefaciens strain MBI600+SX, Bacillusamyloliquefaciens strain D747+SX, Bacillus amyloliquefaciens strainAT-332+SX, Bacillus pumilus+SX, Bacillus pumilus strain GB34+SX,Bacillus pumilus strain QST2808+SX, Bacillus subtilis+SX, Erwiniacarotovora (such as CGE234M403 stain)+SX, Pseudomonas fluorescens (suchas G7090 strain)+SX, Talaromyces flavus (such as SAY-Y-94-01 strain)+SX,Trichoderma atroviride (such as SKT-1 strain)+SX, Trichodermaharzianum+SX, Harpin protein+SX;bupirimate+SX, dimethirimol+SX, ethirimol+SX, hymexazole+SX,octhilinone+SX, oxolinic acid+SX, diethofencarb+SX, zoxamide+SX,pencycuron+SX, fluopicolide+SX, phenamacril+SX, diflumetorim+SX,tolfenpyrad+SX, fentin acetate+SX, fentin chloride+SX, fentinhydroxide+SX, ametoctradin+SX, blasticidin-S+SX, kasugamycin+SX,streptomycin+SX, oxytetracycline+SX, quinoxyfen+SX, proquinazid+SX,chlozolinate+SX, dimethachlone+SX, iprodione+SX, procymidone+SX,vinclozolin+SX, edifenphos+SX, iprobenfos+SX, pyrazophos+SX,isoprothiolane+SX, etridiazole+SX, iodocarb+SX, propamocarb+SX,prothiocarb+SX, aldimorph+SX, dodemorph+SX, fenpropidin+SX,fenpropimorph+SX, piperalin+SX, spiroxamine+SX, tridemorph+SX,fenhexamid+SX, fenpyrazamine+SX, pyributicarb+SX, naftifine+SX,terbinafine+SX, polyoxins+SX, phthalide+SX, pyroquilon+SX,tricyclazole+SX, carpropamid+SX, diclocymet+SX, fenoxanil+SX,tolprocarb+SX, acibenzolar-S-methyl+SX, probenazole+SX, tiadinil+SX,isotianil+SX, laminarin+SX, cymoxanil+SX, fosetyl+SX, teclofthalam+SX,triazoxide+SX, flusulfamide+SX, diclomezine+SX, methasulfocarb+SX,cyflufenamid+SX, metrafenone+SX, pyriofenone+SX, dodine+SX,flutianil+SX, ferimzone+SX, tebufloquin+SX, validamycin+SX, basic copperchloride+SX, copper(II) hydroxide+SX, basic copper sulphate+SX,Dodecylbenzenesulphonic acid bisethylenediamine copper [II] salt(DBEDC)+SX, organocopper+SX, sulfur+SX, chlorothalonil+SX,dichlofluanid+SX, tolylfluanid+SX, guazatine+SX, iminoctadine+SX,anilazine+SX, dithianon+SX, chinomethionat+SX, fluoroimide+SX,dipymetitrone+SX, quinofumelin+SX, dichlobentiazox+SX, fungicidecompound β6+SX, fungicide compound β7+SX, fungicide compound β8+SX,fungicide compound β9+SX, fungicide compound β10+SX, fungicide compoundβ11+SX, fungicide compound β12+SX, fungicide compound β13+SX, fungicidecompound β14+SX, fungicide compound β15+SX, fungicide compound β16+SX,fungicide compound β17+SX, fungicide compound β18+SX;ethephon+SX, chlormequat+SX, chlormequat-chloride+SX, mepiquat+SX,mepiquat-chloride+SX, Gibberellin A3+SX, abscisic acid+SX, Kinetin+SX,benzyladenine+SX, forchlorfenuron+SX, thidiazuron+SX;Glomus spp.+SX, Glomus intraradices+SX, Glomus mosseae+SX, Glomusaggregatum+SX, Glomus etunicatum+SX;Bradyrhizobium elkani+SX, Bradyrhizobium japonicum+SX, Bradyrhizobiumlupini+SX, Rhizobium leguminosarum bv. trifolii+SX, Rhizobiumleguminosarum bv. phaseoli+SX, Rhizobium leguminosarum bv. viciae+SX,Sinorhizobium meliloti+SX, Rhizobium spp.+SX;benoxacor+SX, cloquintocet-mexyl+SX, cyometrinil+SX, dichlormid+SX,fenchlorazole-ethyl+SX, fenclorim+SX, flurazole+SX, furilazole+SX,mefenpyr-diethyl+SX, MG191(2-(dichloromethyl)-2-methyl-1,3-dioxolane)+SX, oxabetrinil+SX,allidochlor+SX, isoxadifen-ethyl+SX, cyprosulfamide+SX, fluxofenim+SX,1,8-naphthalic anhydride+SX, AD-67 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5] decane)+SX.

In the composition of the present invention, the weight ratio of thePresent compound to the present active ingredient includes, for example,usually within a range of 100:1 to 1:100, and preferably within a rangeof 10:1 to 1:10, when the present active ingredient is selected from theabove-mentioned Group (a), Group (c) or Group (d). When the presentactive ingredient is selected from the above-mentioned Group (b), theweight ratio of the Present compound to the present active ingredientincludes, for example, usually within a range of 10,000:1 to 1:100, andpreferably within a range of 1,000:1 to 1:10.

The compound of the present invention and the composition of the presentinvention can be used to control harmful arthropod. Examples of theharmful arthropod are as follows.

Hemiptera pests:

Delphacidae (for example, Laodelphax striatellus, Nilaparvata lugens,Sogatella furcifera, or Peregrinus maidis),

Deltocephalidae (for example, Nephotettix cincticeps, Nephotettixvirescens, Nephotettix nigropictus (Rice green leafhopper), Reciliadorsalis, Empoasca onukii, Empoasca fabae, Dalbulus maidis, Mahanarvaposticata (Sugarcane froghopper), Mahanarva fimbriolota (Sugarcane rootspittlebug), Cofana spectra, or Nephotettix nigropictus, Reciliadorsalis),

Aphididae (for example, Aphis gossypii, Myzus persicae, Brevicorynebrassicae, Aphis spiraecola, Macrosiphum euphorbiae, Aulacorthum solani,Rhopalosiphum padi, Toxoptera citricidus, Hyalopterus pruni, Aphisglycines Matsumura, Rhopalosiphum maidis, Tetraneura nigriabdominalis,Viteus vitifoliae, Daktulosphaira vitifoliae (Grape Phylloxera),Phylloxera devastatrix Pergande (Pecan phylloxera), Phylloxera notabilispergande (Pecan leaf phylloxera), or Phylloxera russellae Stoetzel(Southern pecan leaf phylloxera),

Pentatomidae (for example, Scotinophara lurida, Scotinophara coarctata(Malayan rice black bug), Nezara antennata, Eysarcoris parvus,Halyomorpha mista, Nezara viridula, Euschistus heros (Brown stink bug),Nezara viridula (Southern green stink bug), Piezodorus guildinii (Redbanded stink bug), Scaptocoris castanea (Burrower brown bug), Oebaluspugnax, or Dichelops melacanthus),

Alydidae (for example, Riptortus clavetus, Leptocorisa chinensis,Leptocorisa aceta, or Leptocorisa spp.),

Miridae (for example, Trigonotylus caelestialium, Stenotusrubrovittatus, Lygus lineolaris, or Blissus leucopterus leucopterus(Chinchi bug)),

Aleyrodidae (for example, Trialeurodes vaporariorum, Bemisia tabaci,Dialeurodes citri, or Aleurocanthus spiniferus),

Coccoidea (for example, Aonidiella aurantii, Comstockaspis perniciosa,Unaspis citri, Ceroplastes rubens, Icerya purchasi, PlanococcusKraunhiae, Pseudococcus longispinis, Pseudaulacaspis Pentagona, orBrevennia rehi),

Psyllidae (for example, Diaphorina citri, Psylla pyrisuga, Bactericercacockerelli),

Tingidae (for example, Stephanitis nasi),

Cimicoidea (for example, Cimex lectularius),

Quesada gigas (Giant Cicada);

and the others.

Lepidoptera pests:

Pyralidae (for example, Chilo suppressalis, Chilo polychrysus(Darkheaded stm borer), Tryporyza incertulas, Chilo polychrysus,Scirpophaga innotata, Scirpophaga incertulas (Yellow stem borer),Sesamia inferens (Pink borer), Rupela albinella, Cnaphalocrocismedinalis, Marasmia patnalis, Marasmia exigna, Notarcha derogata, Plodiainterpunctella, Ostrinia furnacalis, Hellula undalis, Pediasiateterrellus, Nymphula depunctalis, Marasmia spp., Hydraecia immanis (Hopvine borer), Ostrinia nubilalis (European corn borer), Elasmopalpuslignosellus (Lesser cornstalk borer), Epinotia aporema (Bean ShootBorer), Diatraea saccharalis (Sugarcane borer), Telchin licus (GiantSugarcane borer)),

Noctuidae (for example, Spodoptera litura, Spodoptera exigua,Pseudaletia separata, Mamestra brassicae, Sesamia inferens, Spodopteramauritia, Spodoptera frugiperda, Spodoptera exempta, Agrotis ipsilon,Plusia nigrisigna, Pseudoplusia includens (Soybean looper), Trichoplusiaspp., Heliothis spp. (for example, Heliothis virescens), Helicoverpaspp. (for example, Helicoverpa armigera), Anticarsia gammatalis(Velvetbean caterpillar), or Alabama argillacea (Cotton leafworm)),

Pieridae (for example, Pieris rapae),

Adokisofiesu genus,

Tortricidae (for example, Grapholita molesta, Leguminivoraglycinivorella, Matsumuraeses azukivora, Adoxophyes orana fasciata,Adoxophyes honmai, Homona magnanima, Archips fuscocupreanus, or Cydiapomonella),

Gracillariidae (for example, Caloptilia theivora, or Phyllonorycterringoneella),

Carposinidae (for example, Carposina niponensis, Ecdytolopha aurantiana(Citrus fruit borer)),

Lyonetiidae (for example, Leucoptera coffeela (Coffee Leaf miner), orLyonetia spp.)),

Lymantriidae (for example, Lymantria spp., or Euproctis spp.),

Yponomeutidae (for example, Plutella xylostella),

Gelechiidae (for example, Pectinophora gossypiella, or Phthorimaeaoperculella),

Arctiidae (for example, Hyphantria cunea);

and the others.

Thysanoptera pests:

Thysanopterae (for example, Frankliniella occidentalis, Thrips parmi,Scirtothrips dorsalis, Thrips tabaci, Frankliniella intonsa,Frankliniella occidentalis, Haplothrips aculeatus, Stenchaetothripsbiformis);

and the others.

Diptera pests:

Diptera:

House mosquitoes (Culex spp.) (for example, Culex pipiens pallens, Culextritaeniorhynchus, or Culex quinquefasciatus),

Aedes spp. (for example, Aedes aegypti, or Aedes albopictus),

Anopheles spp. (for example, Anopheles sinensis),

Chironomidae,

Muscidae (for example, Musca domestica, or Muscina stabulans),

Anthomyiidae (for example, Delia platura, Delia antiqua, or Tetanopsmyopaeformis),

Agromyzidae (for example, Agromyza oryzae, Hydrellia griseola, Liriomyzasativae, Liriomyza trifolii, or Chromatomyia horticola),

Chloropidae (for example, Chlorops oryzae),

Tephritidae (for example, Dacus cucurbitae, or Ceratitis capitata),

Ephydridae (for example, Hydrellia philippina, or Hydrellia sasakii),

Drosophilidae,

Phoridae (for example, Megaselia spiracularis),

Psychodidae (for example, Clogmia albipunctata),

Sciaridae,

Cecidomyiidae (for example, Mayetiola destructor, or Orseolia oryzae),

Diopsidae (for example, Diopsis macrophthalma),

Tipulidae (for example, Tipula oleracea (Common cranefly), or Tipulapaludosa (European cranefly));

and the others.

Coleoptera pests:

Chrysomelidae (for example, Diabrotica virgifera virgifera, Diabroticaundecimpunctata howardi, Diabrotica barberi, Diabrotica virgifera zeae,Diabrotica balteata LeConte, Diabrotica speciosa, Diabrotica speciosa(Cucurbit Beetle), Cerotoma trifurcata, Oulema melanopus, Aulacophorafemoralis, Phyllotreta striolata, Leptinotarsa decemlineata, Oulemaoryzae, Colaspis brunnea, Chaetocnema pulicaria, Epitrix cucumeris,Dicladispa armigera, Stenolophus lecontei (Seedcorn beetle), or Cliviniaimpressifrons (Slender seedcorn beetle)),

Scarabaeidae (for example, Anomala cuprea, Anomala rufocuprea, Popilliajaponica, Rhizotrogus majalis (European Chafer), Bothynus gibbosus(Carrot beetle), Colaspis brunnea (Grape Colaspis), Myochrousdenticollis (southern Corn leaf beetle), Holotrichia spp., orPhyllophaga spp. (for example, Phyllophaga crinita)),

Erirhinidae (for example, Sitophilus zeamais, Echinocnemus squameus,Lissorhoptrus oryzophilus, or Sphenophorus venatus),

Curculionidae (for example, Anthonomus grandis, Sphenophorus callosus(Southern Corn Billbug), Sternechus subsignatus (Soybean stalk weevil),or Sphenophorus spp. (for example, Sphenophorus levis)),

Epilachna (for example, Epilachna vigintioctopunctata),

Scolytidae (for example, Lyctus brunneus, or Tomicus piniperda),

Bostrichidae,

Ptinidae,

Cerambycidae (for example, Anoplophora malasiaca, or Migdolus fryanus),

Elateridae (Agriotes sp., Aelous sp., Anchastus sp., Melanotus sp.,Limonius sp., Conoderus sp., Ctenicera sp.) (for example, Melanotusokinawensis, Agriotes ogurae fuscicollis, or Melanotus legatus),

Staphylinidae (for example, Paederus fuscipes),

Hypothenemus hampei (Coffee Barry Borer);

and the others.

Orthoptera pests:

Locusta migratoria, Gryllotalpa africana, Dociostaurus maroccanus,Chortoicetes terminifera, Nomadacris septemfasciata, Locustana pardalina(Brown Locust), Anacridium melanorhodon (Tree Locust), Calliptamusitalicus (Italian Locust), Melanoplus differentialis (Differentialgrasshopper), Melanoplus bivittatus (Twostriped grasshopper), Melanoplussanguinipes (Migratory grasshopper), Melanoplus femurrubrum (Red-Leggedgrasshopper), Camnula pellucida (Clearwinged grasshopper), Schistocercagregaria, Gastrimargus musicus (Yellow-winged locust), Austracrisguttulosa (Spur-throated locust), Oxya yezoensis, Oxya japonica, Patangasuccincta, Grylloidea (for example, Acheta domesticus, Teleogryllusemma, or Anabrus simplex (Mormon cricket));

and the others.

Hymenoptera pests:

Tenthredinidae (for example, Athalia rosae, or Athalia japonica),

Solenopsis spp.,

Acromyrmex spp. (for example, Atta capiguara (Brown leaf-cutting ant));

and the others.

Blattariae pests:

Blattella germanica, Periplaneta fuliginosa, Periplaneta americana,Periplaneta brunnea, Blatta orientalis, and the others.

Isoptera pests:

Reticulitermes speratus, Coptotermes formosanus, Incisitermes minor(Coptotermes formosanus), Cryptotermes domesticus, Odontotermesformosanus, Neotermes koshunensis, Glyptotermes Satsumensis,Glyptotermes Nakajimai, Glyptotermes Fuscus, Glyptotermes Kodamai,Glyptotermes Kushimensis, Hodotermopsis Sjostedti, Coptotermesguangzhoensis, Reticulitermes amamianus, Reticulitermes miyatakei,Reticulitermes kanmonensis, Nasutitermes takasagoensis, Pericapritermesnitobei, Sinocapritermes mushae, or Cornitermes cumulans);

and the others.

Acarina pests:

Tetranychidae (for example, Tetranychus urticae, Tetranychus kanzawai,Panonychus citri, Panonychus ulmi, Oligonychus spp., or Brevipalpusphoenicis (Southern Turkey spider mites)),

Eriophyidae (for example, Aculops pelekassi, Phyllocoptruta citri,Aculops lycopersici, Calacarus carinatus, Acaphylla theavagrans,Eriophyes chibaensis, or Aculus schlechtendali),

Tarsonemidae (for example, Polyphagotarsonemus latus),

Tenuipalpidae (for Example, Brevipalpus phoenicis),

Tuckerellidae;

Ixodidae (for Example, Haemaphysalis longicornis, Haemaphysalis flava,Dermacentor taiwanicus, Dermacentor variabilis, Ixodes ovatus, Ixodespersulcatus, Ixodes scapularis, Amblyomma americanum, Boophilusmicroplus, or Rhipicephalus sanguineus),

Acaridae (for example, Tyrophagus putrescentiae, or Tyrophagus similis),

Pyroglyphidae (for example, Dermatophagoides farinae, orDermatophagoides ptrenyssnus);

Cheyletidae (for example, Cheyletus eruditus, Cheyletus malaccensis, orCheyletus moorei);

Sarcoptidae (for example, Octodectes cynotis, or Sacroptes scabiei),

Demodex folliculorum (for example, Demodex canis),

Listrophoridae,

Oribatid mites,

Dermanyssidae (for example, Ornithonyssus bacoti, Ornithonyssussylvairum, or Dermanyssus gallinae),

Trombiculid mites (for example, Leptotrombidium akamushi),

and the others.

Araneae:

Chiracanthium japonicum, or Latrodectus hasseltii, and the others.

Chilopoda:

Thereuonema hilgendorfi, or Scolopendra subspinipes, and the others.

Diplopoda:

Oxidus gracilis, or Nedyopus tambanus, and the others,

Isopoda:

Armadillidium vulgare, and the others.

Gastropoda:

Limax marginates, or Limax flavus, Pomacea canaliculata, and the others.

For example, when the present active ingredient is an ingredientselected from the sub group a-9, the composition of the presentinvention can be used to control harmful nematodes. Also, for example,when the present active ingredient is an ingredient selected from thesub group (b), the composition of the present invention can be used tocontrol phytopathogenic fungus.

Examples of the harmful nematodes and the phytopathogenic fungus includethe followings.

Harmful nematodes:

Aphelenchoides sp. (for example, Aphelenchoides basseyi); Pratylenchussp. (for example, Pratylenchus coffeae, Pratylenchus brachyurus,Pratylenchus neglectus); Meloidogyne sp. (for example, Meloidogynejavanica, Meloidogyne incognita, Meloidogyne hapla); Heterodera sp. (forexample, Heterodera glycines); Globodera sp. (for example, Globoderarostochiensis); Bursaphelenchus sp. (for example, Rotylenchulusreniformis, Nothotylenchus acris, Radopholus similis, Ditylenchusdipsaci, Tylenchulus semipenetrans, Longidorus sp., Xiphinema sp.,Trichodorus sp., Bursaphelenchus xylophilus);

Rice diseases: blast (Magnaporthe grisea), brown spot (Cochliobolusmiyabeanus), sheath blight (Rhizoctonia solani), bakanae disease(Gibberella fujikuroi), and downy mildew (Sclerophthora macrospora);

Wheat diseases: powdery mildew (Erysiphe graminis), fusarium blight(Fusarium gaminearum, F. avenaceum, F. culmorum, Microdochium nivale),rust (Puccinia striiformis, P. graminis, P. recondita), snow mould(Micronectriella nivale, M. majus), typhulasnow blight (Typhula sp.),loose smut (Ustilago tritici), stinking smut (Tilletia caries, T.controversa), eyespot (Pseudocercosporella herpotrichoides), leaf blotch(Septoria tritici), glume blotch (Stagonospora nodorum), tan spot(Pyrenophora tritici-repentis), rhizoctonia seeding blight (Rhizoctoniasolani), and take-all disease (Gaeumannomyces graminis);

Barly diseases: powdery mildew (Erysiphe graminis), fusarium blight(Fusarium gaminearum, F. avenaceum, F. culmorum, Microdochium nivale),rust (Puccinia striiformis, P. graminis, P. hordei), loose smut(Ustilago nuda), scald (Rhynchosporium secalis), net blotch (Pyrenophorateres), spot blotch (Cochliobolus sativus), leaf stripe (Pyrenophoragraminea), Ramularia disease (Ramularia collo-cygni), and rhizoctoniaseeding blight (Rhizoctonia solani);

Corn diseases: rust (Puccinia sorghi), southern rust (Pucciniapolysora), northern leaf blight (Setosphaeria turcica), tropical rust(Physopella zeae), southern leaf blight (Cochliobolus heterostrophus),anthracnose (Colletotrichum gfaminicola), gray leaf spot (Cercosporazeae-maydis), eyespot (Kabatiella zeae), phaeosphaeria leaf spot(Phaeosphaeria maydis), diplomat over Deer disease (Stenocarpellamaydis, Stenocarpella macrospora), Stalk Rot (Fusarium graminearum,Fusarium verticilioides, Colletotrichum graminicola), corn smut(Ustilago maydis);

Cotton diseases: anthracnose (Colletotrichum gossypii), grey mildew(Ramuraria areola), alternaria leaf spot (Alternaria macrospora, A.gossypii), Black root rot due to Thielaviopsis spp. (Thielaviopsisbasicola);

Coffee diseases: rust (Hemileia vastatrix), leaf spot (Cercosporacoffeicola);

Rape seed diseases: sclerotinia rot (Sclerotinia sclerotiorum), blackspot (Alternaria brassicae), and black leg (Phoma lingam);

Sugarcane diseases: rust (Puccinia melanocephela, Puccinia kuehnii), andsmut (Ustilago scitaminea);

Sunflower diseases: rust (Puccinia helianthi), and downy mildew(Plasmopara halstedii);

Citrus diseases: melanose (Diaporthe citri), scab (Elsinoe fawcetti),fruit rot (Penicillium digitatum, P. italicum), and epidemics(Phytophthora parasitica, Phytophthora citrophthora);

Apple diseases: blossom blight (Monilinia mali), canker (Valsaceratosperma), powdery mildew (Podosphaera leucotricha), alternaria leafspot (Alternaria alternata apple pathotype), scab (Venturia inaequalis),anthracnose (Glomerella cingulata), brown spot (Diplocarpon mali), ringspot (Botryosphaeria berengeriana), and epidemics (Phytophtoracactorum);

Pear diseases: scab (Venturia nashicola, V. pirina), black spot(Alternaria alternata Japanese pear pathotype) and rust (Gymnosporangiumharaeanum);

Peach diseases: brown rot (Monilinia fructicola), scab (Cladosporiumcarpophilum) and Phomopsis rot (Phomopsis sp.);

Grapes diseases: anthracnose (Elsinoe ampelina), ripe rot (Glomerellacingulata), powdery mildew (Uncinula necator), rust (Phakopsoraampelopsidis), black rot (Guignardia bidwellii), and downy mildew(Plasmopara viticola);

Diseases of Japanese persimmon: anthracnose (Gloeosporium kaki) and leafspot (Cercospora kaki, Mycosphaerella nawae);

Diseases of gourd family: anthracnose (Colletotrichum lagenarium),powdery mildew (Sphaerotheca fuliginea), gummy stem blight (Didymellabryoniae), target spot (Corynespora cassiicola), fusarium wilt (Fusariumoxysporum), downy mildew (Pseudoperonospora cubensis), epidemics(Phytophthora sp.) and damping-off (Pythium sp.);

Tomato diseases: early blight (Alternaria solani), leaf mold(Cladosporium fulvum), leaf mold (Pseudocercospora fuligena), lateblight (Phytophthora infestans), and powdery mildew (Leveillulataurica);

Eggplant disease: brown spot (Phomopsis vexans) and powdery mildew(Erysiphe cichoracearum);

Diseases of Cruciferous Vegetables: alternaria leaf spot (Alternariajaponica), white spot (Cercosporella brassicae), clubroot(Plasmodiophora parasitica), downy mildew (Peronospora parasitica);

Welsh onion diseases: rust (Puccinia allii);

Soybean diseases: purple stain (Cercospora kikuchii), sphaceloma scad(Elsinoe glycines), pod and stem blight (Diaporthe phaseolorum var.sojae), rust (Phakopsora pachyrhizi), target spot (Corynesporacassiicola), anthracnose (Colletotrithum glycines, C. truncatum),Rhizoctonia aerial blight (Rhizoctonia solani), septoria brown spot(Septoria glycines), frog eye leaf spot (Cercospora sojina), sclerotaldisease (Sclerotinia sclerotiorum), Powdery mildew (Microsphaeradiffusa), Stem plague (Phytophthora sojae), downy mildew (Peronosporamanshurica), sudden death (Fusarium virguliforme);

Kindney bean diseases: Crown rot (Sclerotinia sclerotiorum), rust(Uromyces appendiculatus), angular leaf spot (Phaeoisariopsis griseola),and anthracnose (Colletotrichum lindemthianum);

Peanut diseases: early leaf spot (Cercospora personata), late leaf spot(Cercospora arachidicola) and southern blight (Sclerotium rolfsii);

Garden pea diseases: powdery mildew (Erysiphe pisi);

Potato diseases: early blight (Alternaria solani), late blight(Phytophthora infestans), Pink rot (Phytophthora erythroseptica),powdery scab (Spongospora subterranean f. sp. subterranea), andverticillium wilt (verticillium albo-atrum, V. dahliae, V. nigrescens);

Strawberry diseases: powdery mildew (Sphaerotheca humuli);

Tea diseases: net blister blight (Exobasidium reticulatum), white scab(Elsinoe leucospila), gray blight (Pestalotiopsis sp.) and anthracnose(Colletotrichum theae-sinensis);

Tabacco diseases: brown spot (Alternaria longipes), powdery mildew(Erysiphe cichoracearum), anthracnose (Colletotrichum tabacum), downymildew (Peronospora tabacina), and epidemics (Phytophthora nicotianae);

Sugar beet diseases: cercospora leaf spot (Cercospora beticola), leafblight (Thanatephorus cucumeris), root rot (Thanatephorus cucumeris) andaphanomyces root rot (Aphanomyces cochlioides);

Rose diseases: black spot (Diplocarpon rosae) and powdery mildew(Sphaerotheca pannosa);

Diseases of Chrysanthemum: leaf blight (Septoria chrysanthemi-indici)and white rust (Puccinia horiana);

Onion diseases: botrytis leaf blight (Botrytis cinerea, B. byssoidea, B.squamosa), gray-mold neck rot (Botrytis alli), and small sclerotial rot(Botrytis squamosa);

Various crops diseases: gray mold (Botrytis cinerea), and sclerotiniarot (Sclerotinia sclerotiorum);

Diseases of Japanese radish: alternaria leaf spot (Alternariabrassicicola);

Turfgrass diseases: dollar spot (Sclerotinia homeocarpa), brown patchand large patch (Rhizoctonia solani); and

Banana diseases: Sigatoka disease (Mycosphaerella fijiensis,Mycosphaerella musicola);

Seed diseases or diseases in the early stages of the growth of variousplants caused by bacteria of Aspergillus spp., Penicillium spp.,Fusarium spp., Gibberella spp., Tricoderma spp., Thielaviopsis spp.,Rhizopus spp., Mucor spp., Corticium spp., Phoma spp., Rhizoctonia spp.,and Diplodia spp.; and

Viral diseases of various plants mediated by Polymixa genus or Olpidiumgenus.

Burkholderia plantarii of rice (Burkholderia plantarii); Angular LeafSpot of Cucumber (Pseudomonas syringae pv. Lachrymans); wilt disease ofeggplant (Ralstonia solanacearum); Citrus Canker (Xanthomonas citiri);and Sof rot of white cabbage (Erwinia carotovora).

The harmful arthropods, harmful nematodes and phytopathogenic fungus maybe harmful arthropods, harmful nematodes or phytopathogenic fungus whosethe sensitivity to any of the present active ingredient is lowered orwhose the resistance against the present active ingredient is developed.

The compound of the present invention or the composition of the presentinvention can be used to protect plants from the plant diseases causedby insect-mediated viruses.

Examples of the plant diseases caused by the insect-mediated viruses onwhich the compound of the present invention or the composition of thepresent invention has a control efficacy include as follows.

Rice dwarf disease (Rice waika virus), Rice tungro disease (Rice tungrospherical virus, Rice tungro bacilliform virus), Rice grassy stuntdisease (Rice grassy stunt virus), Rice ragged stunt disease (Riceragged stunt virus), Rice stripe disease (Rice stripe virus), Rice blackstreaked dwarf disease (Rice black streaked dwarf virus), Southern riceblack-streaked dwarf disease (Southern rice black-streaked dwarf virus),Rice gall dwarf disease (Rice gall dwarf virus), Rice hoja blancadisease (Rice hoja blanca virus), White leaf desease of rice (Rice whiteleaf virus), Yellow dwarf disease (Yellow dwarf virus), Red disease(Rice penyakit merah virus), Rice yellow stunt disease (Rice yellowstunt virus), Rice transitory yellowing disease (Rice transitoryyellowing virus), Rice Yellow Mottle disease (Rice Yellow Mottle Virus),Rice necrosis mosaic disease (Rice necrosis mosaic virus), Rice dwarfstunt disease (Rice dwarf stunt virus),

Wheat northern cereal mosaic disease (Northern Cereal Mosaic Virus),Barley Yellow Dwarf disease (Barley Yellow Dwarf Virus), Wheat yellowdwarf disease (Wheat yellow dwarf virus), Oat sterile dwarf disease (Oatsterile dwarf virus), Wheat streak mosaic disease (Wheat streak mosaicvirus);

Maize dwarf mosaic disease (Maize dwarf mosaic virus), Maize stripedisease (maize stripe tenuivirus), Maize chlorotic dwarf disease (Maizechlorotic dwarf virus), Maize chlorotic mottle disease (maize chloroticmottle virus), Maize rayado fino disease (maize rayado finomarafivirus), Corn stunt disease (Corn stunt spiroplasma), Maize bushystunt disease (Maize bushy stunt phytoplasma);

Sugarcane mosaic disease (Sugarcane mosaic virus);

Soybean mild mosaic disease (Soybean mild mosaic virus), Mosaic disease(Alfalfa Mosaic Virus, Bean yellow-spot mosaic virus, Soybean mosaicvirus, Bean yellow mosaic virus, Cowpea severe mosaic virus), bean virusdisease (Broad bean wilt virus, Bean common mosaic virus, Peanut stuntvirus, Southern bean mosaic virus), Soybean dwarf disease (Soybean dwarfluteovirus, Milk-vetch dwarf luteovirus), Bean-pod mottle disease(Bean-pod mottle virus), Brazilian bud blight disease (Tobbaco streakvirus), Cowpea chlorotic mottle disease (Cowpea chlorotic mottle), Mungbean yellow mosaic disease (Mung bean yellow mosaic virus), Peanutstripe disease (Peanut stripe mottle), Soybean crinkle leaf disease(Soybean crinkle leaf virus), Soybean severe stunt disease (Soybeansevere stunt virus);

Tomato yellow leaf disease (Tomato chlorosis virus), Tomato spotted wiltdisease (Tomato spotted wilt virus), Tomato yellow leaf curl disease(Tomato yellow leaf curl virus), Melon spotted wilt disease (Melonyellow spot virus), Watermelon mosaic disease (Watermelon mosaic virus),Dwarf disease (Cucumber mosaic virus), Zucchini yellow mosaic disease(Zucchini yellow mosaic virus), Turnip mosaic disease (Turnip mosaicvirus), Cucurbit chlorotic yellow disease (Cucurbit chlorotic yellowsvirus), Capsicum chlorosis disease (Capsicum chlorosis virus), Beetpseudo yellow disease (Beet pseudo yellows virus);

chrysanthemum stem necrosis disease (chrysanthemum stem necrosis virus),Impatiens necrotic spot disease (Impatiens necrotic spot virus), Irisyellow spot disease (Iris yellow spot virus);

Sweet potato mottle mosaic disease (Sweet potato internal cork virus),Sweet potato shukuyo mosaic disease (Sweet potato shukuyo mosaic virus);and

Mosaic virus diseases of various plants mediated by Polymixa spp. orOlpidium spp.

The agent for controlling harmful arthropods of the present inventioncomprises the compound of the present invention or the composition ofthe present invention and an inert active carrier. The agent forcontrolling harmful arthropods is usually prepared by mixing thecompound of the present invention or the composition of the presentinvention with an inert active carrier such as solid carrier, liquidcarrier or gaseous carrier, and if necessary, adding surfactants and theother auxiliary agents for formulation, to formulate into emulsifiableconcentrates, oil solutions, dust formulations, granules, wettablepowders, flowables, microcapsules, aerosols, smoking agents, poisonbaits, resin formulations, shampoo formulations, paste-likeformulations, foams, carbon dioxide formulations and tablets and theothers. Such formulations may be processed into mosquito repellentcoils, electric mosquito repellent mats, liquid mosquito formulations,smoking agents, fumigants, sheet formulations, spot-on formulations orformulations for oral treatment. Also, the agent for controlling harmfularthropods of the present invention may be mixed with other pesticides,miticides, nematicides, fungicides, plant growth regulators, herbicides,and synergists.

The agent for controlling harmful arthropods of the present inventioncomprises usually 0.01 to 95% by weight of the compound of the presentinvention or the composition of the present invention.

The formulation comprising the compound of the present invention and theformulation comprising the active ingredient of the present inventioncan be mixed, and then used as a mixture thereof.

Examples of the solid carrier to be used in the formulation include finepowders or granules of clays (for example, kaolin clay, diatomaceousearth, bentonite, Fubasami clay, or acid white clay), synthetic hydratedsilicon oxides, talcs, ceramics, other inorganic minerals (for example,sericite, quartz, sulfur, active carbon, calcium carbonate or hydratedsilica) or chemical fertilizers (for example, ammonium sulfate, ammoniumphosphate, ammonium nitrate, urea or ammonium chloride) and the others;as well as synthetic resins (for Example, polyester resins such aspolypropylene, polyacrylonitrile, polymethylmethacrylate andpolyethylene terephthalate; nylon resins (for Example, nylon-6, nylon-11and nylon-66); polyamide resins; polyvinyl chloride, polyvinylidenechloride, vinyl chloride-propylene copolymers, and the others).

Examples of the above-mentioned liquid carriers include water; alcohols(for example, methanol, ethanol, isopropyl alcohol, butanol, hexanol,benzyl alcohol, ethylene glycol, propylene glycol or phenoxy ethanol);ketones (for Example, acetone, methyl ethyl ketone or cyclohexanone);aromatic hydrocarbons (for example, toluene, xylene, ethyl benzene,dodecyl benzene, phenyl xylyl ethane or methylnaphthalene); aliphatichydrocarbons (for example, hexane, cyclohexane, kerosene or light oil);esters (for example, ethyl acetate, butyl acetate, isopropyl myristate,ethyl oleate, diisopropyl adipate, diisobutyl adipate or propyleneglycol monomethyl ether acetate); nitriles (for Example, acetonitrile orisobutyronitrile); ethers (for example, diisopropyl ether, 1,4-dioxane,ethyleneglycol dimethyl ether, diethyleneglycol dimethyl ether,diethylene glycol monomethyl ether, propylene glycol monomethyl ether,dipropylene glycol monomethyl ether or 3-methoxy-3-methyl-1-butanol);acid amides (for example, dimethylformamide or dimethylacetamide);halogenated hydrocarbons (for example, dichloromethane, trichloroethaneor carbon tetrachloride); sulfoxides (for example, dimethyl sulfoxide);propylene carbonate; and vegetable oils (for example, soybean oil orcottonseed oil).

Examples of the above-mentioned gaseous carrier include fluorocarbon,butane gas, liquefied petroleum gas (LPG), dimethyl ether, and carbondioxide gas.

Examples of the surfactants include nonionic surfactants such aspolyoxyethylenated alkyl ethers, polyoxyethylenated alkyl aryl ethersand polyethylene glycol fatty acid esters; and anionic surfactants suchas alkyl sulfonates, alkylbenzene sulfonates and alkyl sulfates.

Examples of the other auxiliary agents for formulation include a binder,a dispersant, a colorant and a stabilizer. Specific examples includecasein, gelatin, polysaccharides (for example, starch, gum arabic,cellulose derivatives and alginic acid), lignin derivatives, bentonite,water-soluble synthetic polymers (for example, polyvinyl alcohol,polyvinyl pyrrolidone and polyacrylic acids), PAP (acidic isopropylphosphate), BHT (2,6-di-tert-butyl-4-methylphenol), BHA (a mixture of2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol).

Examples of base material of the resin formulation include polyvinylchloride polymers, polyurethane and the others, and a plasticizer suchas phthalate esters (for example, dimethyl phthalate, dioctylphthalate), adipic acid esters and stearic acid may be added to thesebase materials, if necessary. The resin formulation can be prepared bymixing the compound of the present invention with the above-mentionedbase material, kneading the mixture, followed by molding it by injectionmolding, extrusion molding or pressure molding and the like. Theresultant resin formulation can be subjected to further molding orcutting procedure and the like, if necessary, to be processed intoshapes such as a plate, film, tape, net or string shape. These resinformulations can be processed into animal collars, animal ear tags,sheet products, trap strings, gardening supports and other products.

Examples of a base material for the poison baits include baitingredients such as grain powder, vegetable oil, saccharide andcrystalline cellulose, and if necessary, with addition of antioxidantssuch as dibutylhydroxytoluene and nordihydroguaiaretic acid,preservatives such as dehydroacetic acid, accidental ingestioninhibitors for children and pets such as a chili powder, insectattraction fragrances such as cheese flavor, onion flavor and peanutoil.

The method for controlling harmful arthropods of the present inventionis conducted by applying an effective amount of the compound of thepresent invention or the composition of the present invention to aharmful arthropod directly and/or a habitat thereof (for example, plantbodies, soil, an interior of a house, animal bodies). In the method forcontrolling harmful arthropods of the present invention, the Presentcompound is usually used in the form of a harmful arthropod controllingagent.

When an agent for controlling harmful arthropods of the presentinvention is used for controlling harmful arthropods in an agriculturalfield, the application dose as an amount of the compound of the presentinvention or a total amount of the compound of the present invention andthe active ingredient of the present invention is usually within a rangefrom 1 to 10,000 g per 10,000 m². The emulsifiable concentrate, thewettable powder, or the flowable formulation etc. of an agent forcontrolling harmful arthropods of the present invention is usuallyapplied by diluting it with water in such a way that a concentration ofthe compound of the present invention or a total concentration of thecompound of the present invention and the active ingredient of thepresent invention is within a range from 0.01 to 10,000 ppm. Thegranular formulation, or the dust formulation etc., is usually appliedas itself without diluting it.

When the agent for controlling harmful arthropods of the presentinvention is used to control harmful arthropods that live inside ahouse, the application dose as an amount of the Present compound isusually within a range from 0.01 to 1,000 mg per 1 m² of an area to betreated, in the case of using it on a planar area. In the case of usingit spatially, the application dose as an amount of the Present compoundis usually within a range from 0.01 to 500 mg per m³ of the space to betreated. When the agent for controlling harmful arthropods of thepresent invention is formulated into emulsifiable concentrates, wettablepowders, flowables or the others, such formulations are usually appliedafter diluting it with water in such a way that a concentration of theactive ingredient is within a range from 0.1 to 10,000 ppm, and thensparging it. In the case of being formulated into oil solutions,aerosols, smoking agents, poison baits and the others, such formulationsare used as itself without diluting it.

When the agent for controlling harmful arthropods of the presentinvention is sued for controlling external parasites of livestock suchas cows, horses, pigs, sheep, goats and chickens and small animals suchas dogs, cats, rats and mice, the pest control agent of the presentinvention can be applied to the animals by a known method in theveterinary field. Specifically, when systemic control is intended, thepest control agent of the present invention is administered to theanimals as a tablet, a mixture with feed or a suppository, or byinjection (including intramuscular, subcutaneous, intravenous andintraperitoneal injections). On the other hand, when non-systemiccontrol is intended, the pest control agent of the present invention isapplied to the animals by means of spraying of the oil solution oraqueous solution, pour-on or spot-on treatment, or washing of the animalwith a shampoo formulation, or by putting a collar or ear tag made ofthe resin formulations to the animal. In the case of administering to ananimal body, the dose of the Present compound is usually within a rangefrom 0.1 to 1,000 mg per 1 kg of an animal body weight.

The method for controlling harmful arthropods of the present inventionis carried out by applying an effective amount of the compound of thepresent invention or the composition of the present invention directlyto harmful arthropods, and/or habitats of harmful arthropods. Examplesof the habitats of harmful arthropods include plants, soils forcultivating plants, houses, and animals.

Examples of applying an effective amount of the compound of the presentinvention or the composition of the present invention to plant or soilsfor cultivating plants include a method of applying an effective amountof the compound of the present invention or the composition of thepresent invention to a stem and leaf, a flower, a seedling, an ear of aplant; a method of applying an effective amount of the compound of thepresent invention or the composition of the present invention to a seedor a bulb such as seed tuber (for example, a seed disinfection, a seedsoaking, or a seed coating), or a method of applying an effective amountof the compound of the present invention or the composition of thepresent invention to soils before planting plants or soils afterplanting plants.

Specific examples of applying an effective amount of the compound of thepresent invention or the composition of the present invention to a stemand leaf, a flower, a seedling, an ear of a plant include a method forapplying an effective amount of the compound of the present invention orthe composition of the present invention to a surface of a plant (forexample, foliage application, and trunk application), a method forapplying an effective amount of the compound of the present invention orthe composition of the present invention to a flower or a whole plant atflowering times including before flowering, during flowering, and afterflowering, and a method for applying an effective amount of the compoundof the present invention or the composition of the present invention toan ear or a whole grain at sprouting season of grain.

Examples of a method of controlling harmful arthropods by applying aneffective amount of the compound of the present invention or thecomposition of the present invention soils before planting plants orafter planting plants include a method of applying an effective amountof a composition of the present invention to a root part of a crop to beprotected from damage such as ingestion by harmful arthropods, and amethod of controlling harmful arthropods that ingest a plant bypermeating and transferring an effective amount of the composition ofthe present invention from a root into the interior of the plant body.

Examples of the method of applying an effective amount of the compoundof the present invention or the composition of the present invention tosoils before planting plants or after planting plants include plantinghole treatment (spraying into planting holes, soil mixing after plantinghole treatment), plant foot treatment (plant foot spraying, soil mixingafter plant foot treatment, irrigation at plant foot, plant foottreatment at a later seeding raising stage), planting furrow treatment(planting furrow spraying, soil mixing after planting furrow treatment),planting row treatment (planting row spraying, soil mixing afterplanting row treatment, planting row spraying at a growing stage),planting row treatment at the time of sowing (planting row spraying atthe time of sowing, soil mixing after planting row treatment at the timeof sowing), broadcast treatment (overall soil surface spraying, soilmixing after broadcast treatment), side-article treatment, treatment ofwater surface (application to water surface, application to watersurface after flooding), other soil spraying treatment (spraying of agranular formulation on leaves at a growing stage, spraying under acanopy or around a tree stem, spraying on the soil surface, mixing withsurface soil, spraying into seed holes, spraying on the ground surfacesof furrows, spraying between plants), other irrigation treatment (soilirrigation, irrigation at a seedling raising stage, drug solutioninjection treatment, irrigation of a plant part just above the ground,drug solution drip irrigation, chemigation), seedling raising boxtreatment (spraying into a seedling raising box, irrigation of aseedling raising box, flooding into a seedling raising box with drugsolution), seedling raising tray treatment (spraying on a seedlingraising tray, irrigation of a seedling raising tray, flooding into aseedling raising tray with drug solution), seedbed treatment (sprayingon a seedbed, irrigation of a seedbed, spraying on a lowland ricenursery, immersion of seedlings), seedbed soil incorporation treatment(mixing with seedbed soil, mixing with seedbed soil before sowing,spraying at sowing before covering with soils, spraying at sowing aftercovering with soils, mixing with covering soil, and other treatment(mixing with culture soil, plowing under, mixing with surface soil,mixing with soil at the place where raindrops fall from a canopy,treatment at a planting position, spraying of a granule formulation onflower clusters, mixing with a paste fertilizer).

In a step of applying to a seed or a bulb, a seed described hereinrepresents a seed of a plant at the state before seeding to a soil or aculture medium for cultivating a seed, and a bulb described hereinrepresents discoid stems, corms, rhizomes, tubers, tuberous, seedtubers, and tuberous roots of a plant at the state before planting in asoil or a culture medium for cultivating. A method for controllingharmful arthropods by applying an effective amount of the compound ofthe present invention or the composition of the present invention into aseed or a bulb include a method of applying an effective amount of thecompound of the present invention or the composition of the presentinvention directly into a seed or a bulb of a plant to be protected fromdamage such as ingestion by harmful arthropods; and a method forcontrolling harmful arthropods that ingest a seed by applying aneffective amount of the compound of the present invention or thecomposition of the present invention in the vicinity of a seed or abulb; and a method for controlling harmful arthropods that ingest aplant by permeating and transferring an effective amount of the compoundof the present invention or the composition of the present inventionfrom a seed or a bulb into the interior of the plant body. Examples of amethod of applying an effective amount of the compound of the presentinvention or the composition of the present invention to a seed or abulb include spraying treatment, spray coating treatment, immersiontreatment, impregnation treatment, coating treatment, film coatingtreatment, and pellet coating treatment, and these methods can provide apreparation of a seed or a bulb that retain an effective amount of thecomposition of the present invention or the composition of the presentinvention on the surface and/or into the interior thereof.

When the compound of the present invention or the composition of thepresent invention are applied to a seed or a bulb, an effective amountof the compound of the present invention is usually within a range of0.001 to 100 g, preferably within a range of 0.02 to 20 g, based on 1 kgof the seed or the bulb. Also an effective amount of the composition ofthe present invention is usually within a range of 0.000001 to 50 g,preferably within a range of 0.0001 to 30 g of a total amount of thecompound of the present invention and the active ingredient of thepresent invention, based on 1 kg of the seed or the bulb.

The plants to which the compound of the present invention and thecomposition of the present invention can be applied include thefollowings.

Crops:

corn, rice, wheat, barley, rye, triticale, oat, sorghum, cotton,soybean, peanut, arachis, common bean (kidney bean), lima bean, adzukibean, cowpea, mung bean, urd bean, scarlet runner bean, rice bean, mothbean, tepary bean, broad bean, pea, chick pea, lentils, lupin, pigeonpea, alfalfa, buckwheat, beet, rape, sunflower, sugarcane, tobacco, andthe others;

Vegetables:

solanaceous vegetables (for example, eggplant, tomato, pimento, pepper,bell pepper and potato),

cucurbitaceous vegetables (for example, cucumber, pumpkin, zucchini,water melon, melon, and squash),

cruciferous vegetables (for example, Japanese radish, white turnip,horseradish, kohlrabi, Chinese cabbage, cabbage, leaf mustard, broccoliand cauliflower),

asteraceous vegetables (for example, burdock, crown daisy, artichoke andlettuce),

liliaceous vegetables (for example, green onion, onion, garlic andasparagus),

ammiaceous vegetables (for example, carrot, parsley, celery andparsnip),

chenopodiaceous vegetables (for example, spinach and Swiss chard),

lamiaceous vegetables (for example, Perilla frutescens, mint, basil, andlavender),

strawberry, sweet potato, Dioscorea japonica, colocasia, and the others;

Fruits:

pomaceous fruits (for example, apple, pear, Japanese pear, Chinesequince and quince),

stone fleshy fruits (for example, peach, plum, nectarine, Prunus mume,cherry fruit, apricot and prune),

citrus fruits (for example, Citrus unshiu, orange, lemon, lime andgrapefruit),

nuts (for example, chestnut, walnuts, hazelnuts, almond, pistachio,cashew nuts and macadamia nuts),

berry fruits (for example, blueberry, cranberry, blackberry andraspberry),

grape, kaki persimmon, olive, Japanese plum, banana, coffee, date palm,coconuts,

and the others;

tea, mulberry,

flowering plant,

roadside trees (for example, ash, birch, dogwood, Eucalyptus, Ginkgobiloba, lilac, maple, Quercus, poplar, Judas tree, Liquidambarformosana, plane tree, zelkova, Japanese arborvitae, fir wood, hemlock,juniper, Pinus, Picea, and Taxus cuspidate),

flowers,

ornamental foliage plants,

sods, and

grasses.

The plants described above are not limited specifically, as long as theyare breeds that are usually cultivated.

The plant described above may be plants that are bred by a hybridtechnology.

the plants that are bred by a hybrid technology is a first-generationhybrid that is produced by breeding two kinds of different lines ofbreed variety, and generally speaking, are plants having a heterosishaving superior characters to those of both parents breeds (in general,for example, it leads to enhancement of yield potential and improvementof resistance to biological and abiotic stress factors).

The plants described above may include genetically-modified crop.

For example, the genetically-modified crop described above include alsoplants having resistance to herbicides including HPPD (that is,4-hydroxyphenylpyruvate dioxygenase) inhibitors such as isoxaflutole;ALS (that is, acetoacetate synthase) inhibitors such as imazethapyr andthifensulfuron methyl; EPSP (that is,5-enolpyruvoylshikimate-3-phosphate synthase) inhibitors; glutaminesynthetase inhibitors; PPO (that is, protoporphyrinogen oxidase)inhibitors; bromoxynil; dicamba, and the like, which resistance has beenimparted by a classical breeding method or gene recombinationtechnology.

The plants described above may include plants that have become capableof synthesizing selective toxins and the like (for example, genusBacillus such as Bacillus thuringiensis) produced by using a generecombination technology; and the plants being capable of synthesizing agene segment that match partially an endogenous gene derived from aharmful insect and also impart with specific insecticidal activity byinducing a gene silencing (RNAi; RNA interference) in a target harmfulinsect.

In addition, the plants described above include lines having two or moretypes of characters related to herbicide resistance, pest resistance,disease resistance, and the like as described above, which charactersare imparted using a classical breeding technology or gene recombinationtechnology, and lines having two or more types of properties possessedby parent lines, which properties are imparted by crossinggenetically-engineered plants having the same or different types ofproperties. Examples of such plants include Smart stax (registeredtrademark).

EXAMPLES

The following Examples including Preparation examples, Formulationexamples and Test examples, serve to illustrate the present invention inmore detail, which should not intend to limit the present invention.

First, regarding the preparation of the compound of the presentinvention, the Preparation Examples are shown below.

Preparation Example 1

To a mixture of 2,5-dichloropyrazine 3.0 g, sodium hydride (60%, oily)880 mg, and NMP 50 mL was added benzyl alcohol 2.3 g under ice-cooling.The reaction mixtures were raised to room temperature, and the resultingmixtures stirred at room temperature for 5 hours. To the resultingreaction mixtures was added water, and the mixtures were extracted withethyl acetate. The resulting organic mixtures were washed with saturatedbrine, and dried over anhydrous sodium sulfate, and concentrated underreduced pressure. The resulting residues were subjected to a silica gelcolumn chromatography to give an intermediate compound 1 represented bythe following formula 3.1 g.

Intermediate Compound 1

¹H-NMR (CDCl₃) δ: 8.12 (1H, d), 8.06 (1H, d), 7.46-7.33 (5H, m), 5.37(2H, s).

Preparation Example 2

The mixture of the intermediate compound 1,3.1 g2-[2-fluoro-4-(trifluoromethyl)phenyl]-4,4,5,5-tetramethyl-1,3-2-dioxaborolane4.1 g, tetrakis(triphenylphosphine)palladium(0) 820 mg, and 2M aqueoussodium carbonate solution 18 mL and dimethoxyethane 60 mL was heated at80° C. with stirring for 3 hours. The resulting reaction mixtures wereallowed to stand to room temperature, and to the mixtures was addedwater, and the mixtures were extracted with ethyl acetate. The resultingorganic layers were washed with saturated brine, dried over anhydroussodium sulfate and concentrated under reduced pressure. The resultingresidues were subjected to a silica gel column chromatography to give anintermediate compound 2 represented by the following formula 3.2 g.

Intermediate Compound 2

¹H-NMR (CDCl₃) δ: 8.69 (1H, dd), 8.40 (1H, d), 8.15 (1H, d), 7.56-7.33(7H, m), 5.46 (2H, s).

Preparation Example 3

The mixture of the intermediate compound 2 3.2 g, ethanethiol 680 mg,sodium hydride (60%, oily) 440 mg, and NMP 40 mL was stirred at roomtemperature for 4 fours. To the resulting reaction mixtures was addedwater, and the mixtures were extracted with ethyl acetate. The resultingorganic layers were washed with saturated brine, dried over anhydroussodium sulfate, and concentrated under reduced pressure. The resultingresidues were dissolved into chloroform 50 mL, and to the mixtures wasadded mCPA (75%) 4.6 g under ice-cooling, and the mixtures were stirredfor three hours under ice-cooling. To the resulting reaction mixtureswas added saturated aqueous sodium thiosulfate solution, and themixtures were extracted with chloroform. The resulting organic layerswere washed successively with saturated aqueous sodium hydrocarbonatesolution and saturated brine, dried over anhydrous sodium sulfate, andconcentrated under reduced pressure. The resulting residues weresubjected to a silica gel column chromatography to give an intermediatecompound 3 represented by the following formula 2.8 g.

Intermediate Compound 3

¹H-NMR (CDCl₃) δ: 8.45 (1H, d), 8.29 (1H, d), 8.28 (1H, d), 7.98 (1H,dd), 7.64 (1H, d), 7.51-7.38 (5H, m), 5.45 (2H, s), 3.55 (2H, q), 1.32(3H, t).

Preparation Example 4

The mixture of the intermediate compound 3 2.8 g, boron tribromide (2Mdichloromethane solution) 11 mL, and chloroform 60 mL was stirred for 2hours under ice-cooling. To the resulting reaction mixtures was addedwater, and the mixtures were extracted with chloroform. The resultingorganic layers were washed successively with saturated aqueous sodiumhydrocarbon solution and saturated brine, dried over anhydrous sodiumsulfate, and concentrated under reduced pressure. The resulting residueswere subjected to a silica gel column chromatography to give anintermediate compound c-16 represented by the following formula 20 g.

Intermediate compound c-16

¹H-NMR (DMSO-D₆) δ: 8.24 (1H, s), 8.21 (1H, d), 8.09 (1H, d), 7.88 (1H,d), 7.86 (1H, br s), 3.67 (2H, q), 1.17 (3H, t).

Preparation Example 5

The mixture of the intermediate compound c-16 300 mg, cesium carbonate350 mg, 2,2,2-trifluoroethyl=trifluoromethanesulfonate 230 mg, and NMP 4mL was stirred at room temperature for 2.5 hours. To the resultingreaction mixtures was added water, and the mixtures were extracted withethyl acetate. The resulting organic layers were washed with saturatedbrine, dried over anhydrous sodium sulfate, and concentrated underreduced pressure. The resulting residues were subjected to a silica gelcolumn chromatography to give the Present compound 1 represented by thefollowing formula 220 mg and the side product 1 100 mg.

The Present compounds that are prepared according to the Preparationexample 5 and their physical properties are shown below.

A compound represented by formula (I-1)

wherein A¹, R¹, R^(3b), and n are indicated in Table 6.

TABLE 6 Present compound A¹ R¹ R^(3b) n 1 CH CF₃CH₂ CF₃ 2 2 CHCF₂HCF₂CH₂ CF₃ 2 3 CH CF₃CFHCF₂CH₂ CF₃ 2Present Compound 1

¹H-NMR (CDCl₃) δ: 8.45 (1H, d), 8.38 (1H, d), 8.27 (1H, d), 8.01-7.98(1H, m), 7.63 (1H, d), 4.83 (2H, q), 3.52 (2H, q), 1.32 (3H, t).

Present Compound 2

¹H-NMR (CDCl₃) δ: 8.45 (1H, s), 8.35 (1H, t), 8.28 (1H, t), 7.99 (1H,dd), 7.63 (1H, d), 6.18-5.89 (1H, m), 4.82 (2H, td), 3.52 (2H, q), 1.32(3H, t).

Present Compound 3

¹H-NMR (CDCl₃) δ: 8.45 (1H, d), 8.36 (1H, d), 8.29 (1H, d), 8.00 (1H,dd), 7.63 (1H, d), 5.26-504 (1H, m), 4.87-4.76 (2H, m), 3.52 (2H, q),1.33 (3H, t).

The side products that are prepared according to Preparation example 5and their physical properties are shown below.

A compound represented by formula (B-1)

wherein A¹, R¹, R^(3b), and n are indicated in Table 7.

TABLE 7 Side product A¹ R¹ R^(3b) n 1 CH CF₃CH₂ CF₃ 2 2 CH CF₂HCF₂CH₂CF₃ 2 3 CH CF₃CFHCF₂CH₂ CF₃ 2Side Product 1

¹H-NMR (CDCl₃) δ: 8.43 (1H, s), 8.25 (1H, d), 7.97 (1H, dd), 7.63 (1H,d), 7.42 (1H, s), 4.62 (2H, q), 3.41 (2H, q), 1.30 (3H, t).

Side Product 2

¹H-NMR (CDCl₃) δ: 8.43 (1H, d), 8.24 (1H, d), 7.96 (1H, dd), 7.63 (1H,d), 7.43 (1H, d), 5.96 (1H, tt), 4.58 (2H, t), 3.42 (2H, q), 1.30 (3H,t).

Side Product 3

¹H-NMR (CDCl₃) δ: 8.43 (1H, d), 8.25 (1H, d), 7.96 (1H, dd), 7.63 (1H,d), 7.43 (1H, d), 5.17-4.95 (1H, m), 4.71-4.49 (2H, m), 3.41 (2H, q),1.30 (3H, t).

Preparation Example 6(1)

The mixture of methyl 5-chloro-2-pyridine carboxylate 10 g, sodiummethoxide (28% methanol solution) 28 mL, and THF 100 mL was stirred for3 hours under ice-cooling. To the resulting reaction mixtures was addedethyl methyl sulfone 18 mL under ice-cooling. The reaction mixtures wereraised to 80° C., and heated with stirring for 24 hours. The resultingreaction mixtures were allowed to cool to room temperature and to themixtures was added 2N hydrochloric acid and the mixtures were extractedwith ethyl acetate. The resulting organic layers were dried overanhydrous sodium sulfate and concentrated. The resulting residues weresubjected to a silica gel column chromatography to give the intermediatecompound e-18 represented by the following formula 11 g.

¹H-NMR (CDCl₃) δ: 8.91 (1H, d), 8.25 (1H, d), 4.87 (2H, s), 4.08 (3H,s), 3.29 (2H, q), 1.47 (3H, t).

Preparation Example 6(2)

The mixture of the intermediate compound e-18 5.0 g, ammonium acetate7.89 g, and methanol 15.0 g was heated at 70° C. with stirring for 4hours. The reaction mixtures were concentrated under reduced pressure toobtain the crude product 12.9 g, and thereto was added ethyl acetate 25g to dissolve it. The mixtures were washed with water 15 g three times.The resulting organic layers were concentrated under reduced pressure togive the intermediate compound 18 represented by the following formula4.5 g.

Intermediate Compound 18

¹H-NMR (CDCl₃) δ: 8.52 (1H, d), 8.21 (1H, d), 6.69 (2H, br), 5.31 (1H,s), 4.03 (3H, s), 3.11 (2H, q), 1.41 (3H, t)

Preparation Example 7

To a mixture of DMF 19 mL and chloroform 600 mL was added oxalylchloride 21 mL under ice-cooling. The reaction mixtures were raised toroom temperature, and stirred for 2 hours. To the resulting reactionmixtures was added butyl vinyl ether 64 mL under ice-cooling and themixtures were stirred for 3 hours. To the resulting reaction mixtureswere added the intermediate compound e-18 20 g and triethylamine 68 mL.The reaction mixtures were stirred for 6 hours, and then concentratedunder reduced pressure. To the resulting residues were added ethanol 300mL and 28% aqueous ammonia solution 30 mL. The reaction mixtures wereheated with stirring at 60° C. for 12 hours. The reaction mixtures wereconcentrated under reduced pressure. To the resulting residues was addedwater, and the mixtures were extracted with ethyl acetate. The resultingorganic layers were dried over anhydrous sodium sulfate, andconcentrated under reduced pressure. The resulting residues weresubjected to a silica gel column chromatography to give the intermediatecompound 6 represented by the following formula 11.4 g.

Intermediate Compound 6

¹H-NMR (CDCl₃) δ: 8.74 (1H, dd), 8.66 (1H, dd), 8.49 (1H, d), 8.20 (1H,d), 7.55 (1H, dd), 4.05 (3H, s), 3.85 (2H, q), 1.38 (3H, t).

Preparation Example 8

The mixture of the intermediate compound 6 4.5 g, and 12N hydrochloricacid 20 mL was heated at 100° C. with stirring for 1 hour. The reactionmixtures were allowed to cool to room temperature, and thereto was addedice water 100 mL. The solution was alkalified with saturated aqueoussodium hydrocarbon solution, and the mixtures were extracted with ethylacetate. The resulting organic layers were dried over anhydrous sodiumsulfate, and concentrated under reduced pressure. The resulting residueswere subjected to a silica gel column chromatography to give theintermediate compound c-2 represented by the following formula 4.3 g.

The compounds that prepared according to the method described inPreparation example 8 and their physical properties are shown below.

A compound represented by formula (M-3-1)

wherein A¹, R^(3b), and n are indicated in Table 8.

TABLE 8 Intermediate compound A¹ R^(3b) n c-2 N H 2 11 N H 0Intermediate Compound c-2

¹H-NMR (CDCl₃) δ: 8.81 (1H, dd), 8.47 (1H, dd), 8.21 (1H, d), 7.97 (1H,d), 7.52 (1H, dd), 3.83 (2H, q), 1.39 (3H, t).

Intermediate Compound 11

¹H-NMR (CDCl₃) δ: 8.40 (1H, dd), 8.34 (1H, d), 8.04 (1H, br s), 7.69(1H, dd), 7.24 (1H, dd), 2.94 (2H, q), 1.34 (3H, t).

Preparation Example 9

The mixture of the intermediate compound c-2 4.3 g, phosphorusoxychloride 12 mL, and toluene 60 mL was heated at 100° C. with stirringfor 2 hours. The resulting reaction mixtures were allowed to cool toroom temperature, and concentrated under reduced pressure. To theresulting residues was added water, and the mixtures were extracted withchloroform. The resulting organic layers were dried over anhydroussodium sulfate and concentrated under reduced pressure to give theintermediate compound d-2 represented by the following formula 4.6 g.

The compounds that prepared according to the method described inPreparation example 9 and their physical properties are shown below.

A compound represented by formula (M-4-1)

wherein V, A¹, R^(3b) and n are indicated in Table 9.

TABLE 9 Intermediate compound V A¹ R^(3b) n d-2 Cl N H 2 12 Cl N H 0 13Br N H 2Intermediate Compound d-2

¹H-NMR (CDCl₃) δ: 8.94 (1H, dd), 8.90 (1H, dd), 8.59 (1H, d), 8.52 (1H,d), 7.65 (1H, dd), 3.81 (2H, q), 1.39 (3H, t).

Intermediate Compound 12

¹H-NMR (CDCl₃) δ: 9.10 (1H, d), 8.68 (1H, d), 8.49 (1H, dd), 7.75 (1H,dd), 7.33 (1H, dd), 2.94 (2H, q), 1.33 (3H, t).

Intermediate Compound 13

¹H-NMR (CDCl₃) δ: 8.91 (1H, d), 8.87 (1H, s), 8.67 (1H, s), 8.50 (1H,d), 7.62 (1H, q), 3.78 (2H, q), 1.37 (3H, t)

Preparation Example 10

The mixture of the intermediate compound d-2 300 mg, cesium carbonate480 mg, 2,2,3,3-tetrafluoropropanol 210 mg, and NMP 4 mL was heated at70° C. with stirring for 2 hours. The resulting reaction mixtures wereallowed to cool to room temperature, and thereto was added water, andthe mixtures were extracted with ethyl acetate. The resulting organiclayers were washed successively with saturated brine, dried overanhydrous sodium sulfate and concentrated. The resulting residues weresubjected to a silica gel column chromatography to give the Presentcompound 4 represented by the following formula 300 mg.

The compounds that prepared according to the method described inPreparation example 10 and their physical properties are shown below.

A compound represented by formula (I-1)

wherein A¹, R¹, R^(3b) and n are indicated in Table 10.

TABLE 10 Pres- ent com- pound A¹ R¹ R^(3b) n 4 N CF₂HCF₂CH₂ H 2 5 NCF₃CF₂CH₂ H 2 6 N CF₃CFHCF₂CH₂ H 2 7 N

H 2 8 N CF₃CH₂ H 2 9 N CF₂HCH₂ H 2 10 N CH₃CF₂CH₂ H 2 11 N CF₃CH(CH₃) H2 12 N CF₃CF₂CH(CH₃) H 2 13 N CF₃CF₂CF₂CH₂ H 2 14 N

H 2 15 N CF₃CF₂CF₂CF₂CH₂ H 2 16 N CF₃CF₂CF₂CH(CH₃) H 2 17 N

H 2 18 N CCl₃CH₂ H 2 19 N CF₃CH═CHCH₂ H 2 20 N CF₃SCH₂CH₂ H 2 21 NCF₃OCH₂CH₂ H 2 22 N CF₃CCl₂CH₂ H 2 23 N CF3C≡CCH₂ H 2 24 N

H 2 25 N CF₃CH═CFCH₂ H 2 26 N CF₃CF₂CH₂ CF₃ 2 27 N CF₂HCF₂CH₂ CF₃ 2 28 NCF₃CFHCF₂CH₂ CF₃ 2 29 N CF₃CF₂CF₂CH₂ CF₃ 2 30 N CF₃CH(CH₃) CF₃ 2 31 NCF₃CF₂CH(CH₃) CF₃ 2 32 N CF₃CF₂CF₂CH(CH₃₎ CF₃ 2Present Compound 4

¹H-NMR (CDCl₃) δ: 8.90 (1H, dd), 8.66 (1H, d), 8.50 (1H, dd), 8.31 (1H,d), 7.59 (1H, dd), 6.03 (1H, tt), 4.83 (2H, tt), 3.83 (2H, q), 1.38 (3H,t).

Present Compound 5

¹H-NMR (CDCl₃) δ: 8.90 (1H, dd), 8.66 (1H, d), 8.50 (1H, dd), 8.33 (1H,d), 7.59 (1H, dd), 4.91 (2H, td), 3.83 (2H, q), 1.38 (3H, t).

Present Compound 6

¹H-NMR (CDCl₃) δ: 8.91 (1H, dd), 8.67 (1H, d), 8.50 (1H, dd), 8.32 (1H,d), 7.59 (1H, dd), 5.27-5.03 (1H, m), 4.89-4.78 (2H, m), 3.83 (2H, q),1.39 (3H, t).

Present Compound 7

¹H-NMR (CDCl₃) δ: 8.91-8.88 (1H, m), 8.63 (1H, d), 8.49 (1H, dd), 8.22(1H, d), 7.56 (1H, dd), 4.59-4.39 (2H, m), 3.85 (2H, q), 2.25-2.12 (1H,m), 1.41-1.29 (5H, m).

Present Compound 8

¹H-NMR (CDCl₃) δ: 8.89 (1H, d), 8.64 (1H, s), 8.49 (1H, d), 8.32 (1H,$),7.57 (1H, dd), 4.83 (2H, q), 3.82 (2H, q), 1.37 (3H, t),

Present Compound 9

¹H-NMR (CDCl₃) δ: 8.89 (1H, d), 8.63 (1H, s), 8.48 (1H, d), 8.28 (1H,s), 7.56 (1H, dd), 6.16 (1H, tt), 4.62 (2H, td), 3.82 (2H, q), 1.37 (3H,t)

Present Compound 10

¹H-NMR (CDCl₃) δ: 8.89 (1H, d), 8.63 (1H, s), 8.48 (1H, d), 8.28 (1H,s), 7.54-7.58 (1H, m), 4.58 (2H, t), 3.83 (2H, q), 1.77 (3H, t), 1.37(3H, t)

Present Compound 11

¹H-NMR (CDCl₃) δ: 8.90 (1H, dd), 8.64 (1H, d), 8.50 (1H, dd), 8.27 (1H,d), 7.58 (1H, dd), 5.84-5.74 (1H, m), 3.84 (2H, m), 1.56 (3H, d), 1.39(3H, t).

Present Compound 12

¹H-NMR (CDCl₃) δ: 8.90 (1H, dd), 8.65 (1H, d), 8.51 (1H, dd), 8.26 (1H,d), 7.58 (1H, dd), 5.90 (1H, dq), 3.85 (2H, m), 1.58 (3H, d), 1.39 (3H,t).

Present Compound 13

¹H-NMR (CDCl₃) δ: 8.88 (1H, dd), 8.64 (1H, d), 8.48 (1H, dd), 8.31 (1H,d), 7.57 (1H, dd), 4.93 (2H, t), 3.81 (2H, q), 1.36 (3H, t).

Present Compound 14

¹H-NMR (CDCl₃) δ: 8.89 (1H, dd), 8.61 (1H, d), 8.50 (1H, dd), 8.28 (1H,d), 7.57 (1H, dd), 5.28 (1H, m), 3.92-3.79 (2H, m), 1.39 (3H, t),1.34-1.28 (1H, m), 0.82-0.62 (4H, m).

Present Compound 15

¹H-NMR (CDCl₃) δ: 1.38 (3H, q), 3.82 (2H, q), 4.96 (2H, t), 7.57 (1H,dd), 8.32 (1H, s), 8.49 (1H, d), 8.65 (1H, s), 8.89 (1H, d)

Present Compound 16

¹H-NMR (CDCl₃) δ: 1.37 (3H, m), 1.54 (3H, m), 3.80-3.88 (2H, m),5.88-6.00 (1H, m), 7.57 (1H, dd), 8.24 (1H, s), 8.50 (1H, d), 8.65 (1H,s), 8.88 (1H, d)

Present Compound 18

¹H-NMR (CDCl₃) δ: 1.38 (3H, t), 3.83 (2H, q), 5.11 (2H, s), 7.53-7.63(1H, m), 8.37 (1H, s), 8.49 (1H, d), 8.65 (1H, s), 8.89 (1H, d)

Present Compound 19

¹H-NMR (CDCl₃) δ: 1.38 (3H, t), 3.06-3.18 (2H, m), 3.82 (2H, d),4.99-5.09 (1H, m), 7.53-7.66 (2H, m), 8.32 (1H, s), 8.49 (1H, d), 8.65(1H, d), 8.89 (1H, s)

Present Compound 24

¹H-NMR (CDCl₃) δ 0.92 (2H, s), 1.18 (2H, s), 1.36 (3H, t), 3.82 (2H, q),4.51 (2H, s), 7.53-7.56 (1H, m), 8.22 (1H, s), 8.47 (1H, d), 8.60 (1H,s), 8.87 (1H, d)

Preparation Example 11

The mixture of 2-bromo-5-methoxypyradine 4.9 g,(3-fluoropyridin-2-yl)tributyltin 14 g,tetrakis(triphenylphosphine)palladium(0) 0.60 g, and copper(I) iodide1.0 g, lithium chloride 1.7 g, and toluene 60 mL was heated under refluxwith stirring for 10 hours. The resulting reaction mixtures were allowedto cool to room temperature, and thereto was added water, and themixtures were extracted with ethyl acetate. The resulting organic layerswere washed with saturated brine, dried over anhydrous sodium sulfate,and concentrated. The resulting residues were subjected to a silica gelcolumn chromatography to give the intermediate compound 9 represented bythe following formula 5.2 g.

Intermediate Compound 9

¹H-NMR (CDCl₃) δ: 8.80 (1H, s), 8.61-8.58 (1H, m), 8.41 (1H, d),7.59-7.53 (1H, m), 7.39-7.33 (1H, m), 4.05 (3H, s).

Preparation Example 12

To the mixture of the intermediate compound 9 5.2 g, sodium hydride(60%, oily), and DMF 85 mL was added ethanethiol 1.7 g underice-cooling. The resulting mixtures were stirred at room temperature for3 hours. To the resulting reaction mixtures was added water, and themixtures were extracted with ethyl acetate. The resulting organic layerswere washed with saturated brine, dried over anhydrous sodium sulfate,and concentrated. The resulting residues were subjected to a silica gelcolumn chromatography to give the intermediate compound 10 representedby the following formula 4.4 g.

Intermediate Compound 10

¹H-NMR (CDCl₃) δ: 8.75 (1H, d), 8.46 (1H, dd), 8.32 (1H, d), 7.71 (1H,dd), 7.27 (1H, dd), 4.04 (3H, s), 2.92 (2H, q), 1.31 (3H, t).

Preparation Example 13

The mixture of the intermediate compound 12 2.9 g, mCPBA (75%) 5.6 g,and chloroform 40 mL was stirred under ice-cooling for 4 hours. To theresulting reaction mixtures was added saturated aqueous sodiumthiosulfate solution, and the mixtures were extracted with chloroform.The resulting organic layers were washed successively with saturatedaqueous sodium hydrocarbon solution, water, and saturated brine, driedover anhydrous sodium sulfate, and concentrated under reduced pressure.The resulting residues were subjected to a silica gel columnchromatography to give the intermediate compound d-2 2.8 g.

Preparation Example 14-1

To the mixture of magnesium chloride 5.16 g, triethylamine 9.15 g andTHF 24 g was added 1-ethanesulfonyl-2-propanone 8.15 g at roomtemperature and the mixtures were stirred for 1 hour. To the mixtureswas added dropwise a mixture of 5-chloro-2-pyradine carboxylic acidchloride 8.0 g and ThF 8 g over 30 minutes, and the mixtures werestirred at room temperature for 3 hours. To the mixtures was added 13%hydrochloric acid 25 g, and the mixtures were stirred for another 17hours. The resulting mixtures were extracted with toluene 40 g, and theorganic layers were washed with water twice (water 16 g, water 8 g,successively). The resulting organic layers were concentrated underreduced pressure. The resulting residues were recrystallized fromtoluene 8 g to give the intermediate compound e-16 represented by thefollowing formula 9.16 g.

Intermediate Compound e-16

¹H-NMR (CDCl₃) δ: 9.08 (1H, d), 8.70 (1H, d), 4.89 (2H, s), 3.29 (2H,q), 1.48 (3H, t)

Preparation Example 14-2

The compounds that prepared according to the method described inPreparation example 14-1 and their physical properties are shown below.

Intermediate Compound e-24

¹H-NMR (CDCl₃) δ: 8.90 (1H, d), 8.40 (1H, d), 4.95 (2H, td), 4.88 (2H,s), 3.29 (2H, q), 1.47 (3H, t).

Preparation Example 15-1

The mixture of the intermediate compound e-16 2.2 g, ammonium acetate3.4 g and methanol 10 g was stirred at 70° C. for 3 hours. The mixtureswere cooled to room temperature, and thereto was added water, and themixtures were extracted with ethyl acetate. The resulting organic layerswere washed with water 10 g, dried over anhydrous sodium sulfate, andconcentrated under reduced pressure to give the intermediate compoundf-16 represented by the following formula 1.6 g.

Intermediate Compound f-16

¹H-NMR (DMSO-d6) δ: 9.05 (1H, d), 8.89 (1H, d), 7.01 (2H, br), 5.67 (1H,s), 3.09 (2H, q), 1.23 (3H, t)

The compounds that prepared according to the method described inPreparation example 15-1 and their physical properties are shown below.

¹H-NMR (CDCl₃) δ: 8.52 (1H, d), 8.35 (1H, d), 6.68 (1H, s), 5.34 (1H,s), 4.91 (2H, td), 3.11 (2H, q), 1.41 (3H, t).

Preparation Example 16(1)

To the mixtures of the intermediate compound f-16 1.0 g, acetic acid0.27 g, and methanol 3.0 g was added acrolein 0.27 g at 60° C., and themixtures were stirred for 5 hours. To the mixtures was added acrolein0.045 g, and the mixtures were stirred for another 3 hours. The mixtureswere concentrated under reduced pressure to give the intermediatecompound 16 represented by the following formula 1.3 g.

Intermediate Compound 16

¹H-NMR (CDCl₃) δ: 8.54 (2H, m), 5.12 (1H, s), 4.60 (1H, q), 3.41 (3H,s), 2.95 (2H, m), 2.67 (1H, m), 2.53 (1H, m), 2.22 (1H, m), 1.77 (1H,m), 1.24 (3H, t)

Preparation Example 16(2)

The intermediate compound 19 represented by the following formula wasobtained by using the intermediate compound 18 instead of theintermediate compound f-16 according to the method described inPreparation example 16(1).

Intermediate Compound 19

¹H-NMR (CDCl₃) δ: 8.31 (1H, d), 8.15 (1H, d), 5.21 (1H, br), 4.59 (1H,m), 4.00 (3H, s), 3.37 (3H, s), 2.94 (2H, m), 2.67 (1H, m), 2.52 (1H,m), 2.19 (1H, m), 1.75 (1H, m), 1.22 (3H, t)

Preparation Example 17

The intermediate compound 16 0.10 g, vinyl acetate 0.16 g and aceticacid 1.0 g and 5% Pd—C 0.010 g were mixed, and the reaction vessel wasreplaced with nitrogen gas, and the mixtures were heated at 60° C. withstirring for 3 hours, and heated at 100° C. with stirring for 2 hours.The resulting reaction mixtures were analyzed by a high performanceliquid chromatography and confirmed that contained 21% area percentageof the intermediate compound d-2.

Preparation Example 18

To the mixtures of the intermediate compound e-16 50 g, triethylamine0.41 g, methanol 12.5 g, and toluene 12.5 g was added acrolein 1.35 g atroom temperature, and the mixtures were stirred for 1 hour. It wasconfirmed by ¹H-NMR that the mixtures contained the intermediatecompound 17.

Intermediate Compound 17

¹H-NMR (CDCl₃) δ: 9.73 (1H, s), 9.08 (1H, d), 8.66 (1H, d), 5.83 (1H,dd), 3.17 (2H, m), 2.60 (2H, m), 2.50 (2H, m), 1.41 (3H, t)

Without isolating the intermediate compound 17, to the resultingreaction mixtures was added ammonium acetate 1.86 g, and the mixtureswere stirred at room temperature for 7 hours. To the resulting reactionmixtures were added water 10 g, and the mixtures were extracted withethyl acetate 250 g. The resulting organic layers were washed with water10 g, and concentrated under reduced pressure to give the intermediatecompound 16 6.0 g.

Preparation Example 19

The mixture of the intermediate compound 19 50 g, THF 10.0 g andmethanesulfonyl chloride 0.50 g was stirred at 60° C. for 3 hours. Theresulting reaction mixtures were analyzed by a high performance liquidchromatography and confirmed that the mixtures contained 29% areapercentage of the intermediate compound 6.

Preparation Example 20

The mixtures of the intermediate compound 20 20 g,2,2,3,3,3-hexafluoropropanol 0.61 mL, cesium carbonate 20 g and DMF 20mL was stirred at 40° C. for 3 hours. The reaction mixtures were addedto 1N hydrochloric acid and the mixtures were extracted with ethylacetate. The resulting organic layers were dried over anhydrous sodiumsulfate, and concentrated under reduced pressure. The resulting residueswere subjected to a silica gel column chromatography to give the Presentcompound 343 1.9 g as a crude product.

Intermediate Compound 20

¹H-NMR (CDCl₃) δ: 8.84 (1H, d), 8.63 (1H, d), 8.55 (1H, d), 8.03 (1H,d), 7.48-7.30 (5H, m), 5.27 (2H, s), 3.84-3.77 (2H, m), 1.32 (3H, t).

Present Compound 343

¹H-NMR (CDCl₃) δ: 8.61 (1H, d), 8.58 (1H, d), 8.30 (1H, d), 8.03 (1H,d), 7.48-7.36 (5H, m), 5.26 (2H, s), 4.89 (2H, td), 3.80 (2H, q), 1.31(3H, t).

Preparation Example 21

The mixtures of the Present compound 343 1.9 g as crude product, and HBrin acetic acid 4 mL was stirred at 70° C. for 2 hours. To the reactionmixtures was added water, and the mixtures were extracted with ethylacetate. The resulting organic layers were dried over anhydrous sodiumsulfate, and concentrated under reduced pressure. The resulting residueswere subjected to a silica gel column chromatography to give the Presentcompound 344 1.0 g.

Present Compound 344

¹H-NMR (CDCl₃) δ: 8.59 (1H, d), 8.53 (1H, d), 8.30 (1H, d), 7.99 (1H,d), 4.90 (2H, dd), 3.85 (2H, q), 1.39 (3H, t).

Preparation Example 22

The mixture of the Present compound 344 0.33 g, isopropyl iodide 0.12mL, cesium carbonate 390 mg, and DMF 2 mL was stirred at roomtemperature for 1 hour. To the reaction mixtures was added water, andthe mixtures were extracted with MTBE. The resulting organic layers weredried over anhydrous sodium sulfate, and concentrated under reducedpressure. The resulting residues were subjected to a silica gel columnchromatography to give the Present compound 279 0.26 g.

Present Compound 279

¹H-NMR (CDCl₃) δ: 8.57 (1H, d), 8.51 (1H, d), 8.30 (1H, d), 7.93 (1H,d), 4.89 (2H, t), 4.78-4.72 (1H, m), 3.82 (2H, q), 1.43 (6H, d), 1.38(3H, t).

Preparation Example 23

The compounds that prepared according to the method described inPreparation example 22 and their physical properties are show below.

Present Compound 274

¹H-NMR (CDCl₃) δ: 8.58 (1H, d), 8.55 (1H, d), 8.30 (1H, d), 7.94 (1H,d), 4.90 (2H, t), 4.23 (2H, q), 3.82 (2H, q), 1.51 (3H, t), 1.38 (3H,t).

Present Compound 339

¹H-NMR (CDCl₃) δ: 8.57 (1H, d), 8.55 (1H, d), 8.30 (1H, d), 7.94 (1H,d), 4.89 (2H, t), 4.11 (2H, t), 3.82 (2H, q), 1.92-1.88 (2H, m), 1.38(3H, t), 1.10 (3H, t).

Present Compound 340

¹H-NMR (CDCl₃) δ: 8.58 (1H, d), 8.55 (1H, d), 8.28 (1H, d), 7.94 (1H,d), 6.02 (1H, tt), 4.81 (2H, tt), 4.11 (2H, t), 3.82 (2H, q), 1.90 (2H,td), 1.38 (3H, t), 1.09 (3H, t).

Present Compound 280

¹H-NMR (CDCl₃) δ: 8.58 (1H, d), 8.51 (1H, d), 8.28 (1H, d), 7.93 (1H,d), 6.02 (1H, tt), 4.85-4.70 (3H, m), 3.82 (2H, q), 1.43 (6H, d), 1.38(3H, t).

Preparation Example 24

The mixture of the Present compound 345 1.4 g, N-bromosuccinimide 680mg, and acetic acid 7 mL was heated under reflux with stirring for 24hours. The resulting mixtures were made pH 11 with 1N sodium hydroxide.To the mixtures was added saturated aqueous sodium sulfite solution, andthe precipitated solids were filtered and washed with water to give thePresent compound 346 860 mg.

Present Compound 345

¹H-NMR (CDCl₃) δ: 8.52 (1H, d), 8.40 (1H, d), 8.01 (1H, d), 6.63 (1H,d), 4.93 (2H, t), 3.39 (2H, q), 1.31 (3H, t).

Present Compound 346

¹H-NMR (CDCl₃) δ: 8.63 (1H, s), 8.42 (1H, s), 8.38 (1H, s), 4.93 (2H,t), 3.36-3.27 (2H, m), 1.32 (3H, t).

Preparation Example 25

The mixtures of the Present compound 346 860 mg, 4-fluorophenyl boronicacid 270 mg, tetrakis(triphenylphosphine)palladium(0) 32 mg,2-dicyclohexylphosphino-2′-6′-dimethoxybiphenyl 57 mg, tripotassiumphosphate 1.5 g, and dimethoxyethane 4.5 mL and was heated under refluxwith stirring for 10 hours. To the resulting mixtures was added water,and the mixtures were extracted with ethyl acetate. The resultingorganic layers were dried over anhydrous sodium sulfate, andconcentrated under reduced pressure. The resulting residues weresubjected to a silica gel column chromatography to give the Presentcompound 347 280 mg.

Present Compound 347

¹H-NMR (DMSO-D₆) δ: 8.64 (1H, d), 8.60 (1H, d), 7.95 (1H, s), 7.85 (2H,dd), 7.33-7.28 (2H, m), 5.27 (2H, t), 3.50-3.39 (2H, m), 1.23-1.15 (3H,m).

Preparation Example 26

The mixtures of the Present compound 347 280 mg, and phosphorusoxychloride 5 mL was heated under reflux with stirring for 72 hours. Theresulting reaction mixtures were concentrated under reduced pressure. Tothe resulting residues were added saturated aqueous sodium hydrocarbonsolution under ice-cooling and the mixtures were extracted with ethylacetate. The resulting organic layers were dried over anhydrous sodiumsulfate, and concentrated under reduced pressure. The resulting residueswere subjected to a silica gel column chromatography to give the Presentcompound 348 130 mg.

Present Compound 348

¹H-NMR (CDCl₃) δ: 8.75 (1H, d), 8.43 (1H, s), 8.35 (1H, d), 7.57-7.51(2H, m), 7.26-7.19 (2H, m), 4.93 (2H, t), 3.89 (2H, q), 1.42 (3H, t).

Preparation Example 27

The mixtures of the intermediate compound e-24 390 mg, the intermediatecompound 21 200 mg, sodium hydride (60%, oily) 95 mg, and THF 5 mL wasstirred under ice-cooling for 24 hours. To the resulting reactionmixtures were added ammonium acetate 830 mg and ethanol 5 mL underice-cooling. The resulting reaction mixtures were stirred at 80° C. for24 hours. The resulting reaction mixtures were concentrated underreduced pressure, and the resulting residues were subjected to a silicagel column chromatography to give the Present compound 194 120 mg.

Present Compound 194

¹H-NMR (CDCl₃) δ: 9.07 (1H, d), 8.71 (1H, d), 8.63 (1H, d), 8.35 (1H,d), 7.69-7.66 (2H, m), 7.28-7.25 (2H, m), 4.92 (2H, td), 3.89 (2H, q),1.45-1.40 (3H, m).

The compounds represented by formula (100)

[wherein, R³⁰¹, R³⁰², R³⁰³, R⁶⁰¹, R⁶⁰², R¹⁰⁰, and A¹ represent any oneof the combination indicated in the following Table 11 to Table 36]can be prepared according to the processes described above.

TABLE 11 Present compound A¹ R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² 33 N CF₂HCH₂H H NH₂ H H 34 N CF₃CF₂CH₂ H H NH₂ H H 35 N CF₂HCF₂CH₂ H H NH₂ H H 36 NCF₃CF₂CF₂CH₂ H H NH₂ H H 37 N CF₃CFHCF₂CH₂ H H NH₂ H H 38 N CF₂HCH₂ H HNHCH₃ H H 39 N CF₃CF₂CH₂ H H NHCH₃ H H 40 N CF₂HCF₂CH₂ H H NHCH₃ H H 41N CF₃CF₂CF₂CH₂ H H NHCH₃ H H 42 N CF₃CFHCF₂CH₂ H H NHCH₃ H H 43 NCF₂HCH₂ H H N (CH₃)₂ H H 44 N CF₃CF₂CH₂ H H N (CH₃)₂ H H 45 N CF₂HCF₂CH₂H H N (CH₃)₂ H H 46 N CF₃CF₂CF₂CH₂ H H N (CH₃)₂ H H 47 N CF₃CFHCF₂CH₂ HH N (CH₃)₂ H H 48 N CF₂HCH₂ H H N (CH₂CH₃)₂ H H 49 N CF₃CF₂CH₂ H H N(CH₂CH₃)₂ H H 50 N CF₂HCF₂CH₂ H H N (CH₂CH₃)₂ H H 51 N CF₃CF₂CF₂CH₂ H HN (CH₂CH₃)₂ H H 52 N CF₃CFHCF₂CH₂ H H N (CH₂CH₃)₂ H H 53 N CF₂HCH₂ H HNHCH₂CF₃ H H 54 N CF₃CF₂CH₂ H H NHCH₂CF₃ H H 55 N CF₂HCF₂CH₂ H HNHCH₂CF₃ H H 56 N CF₃CF₂CF₂CH₂ H H NHCH₂CF₃ H H 57 N CF₃CFHCF₂CH₂ H HNHCH₂CF₃ H H

TABLE 12 Present compound A¹ R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² 58 N CF₂HCH₂H H Cl H H 59 N CF₃CF₂CH₂ H H Cl H H 60 N CF₂HCF₂CH₂ H H Cl H H 61 NCF₃CF₂CF₂CH₂ H H Cl H H 62 N CF₃CFHCF₂CH₂ H H Cl H H 63 N CF₂HCH₂ H Cl HH H 64 N CF₃CF₂CH₂ H Cl H H H 65 N CF₂HCF₂CH₂ H Cl H H H 66 NCF₃CF₂CF₂CH₂ H Cl H H H 67 N CF₃CFHCF₂CH₂ H Cl H H H 68 N CF₂HCH₂ H HOCH₃ H H 69 N CF₃CF₂CH₂ H H OCH₃ H H 70 N CF₂HCF₂CH₂ H H OCH₃ H H 71 NCF₃CF₂CF₂CH₂ H H OCH₃ H H 72 N CF₃CFHCF₂CH₂ H H OCH₃ H H

TABLE 13 Present compound A¹ R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² 73 N CF₂HCH₂H H

H H 74 N CF₃CF₂CH₂ H H

H H 75 N CF₂HCF₂CH₂ H H

H H 76 N CF₃CF₂CF₂CH₂ H H

H H 77 N CF₃CFHCF₂CH₂ H H

H H 78 N CF₂HCH₂ H H

H H 79 N CF₃CF₂CH₂ H H

H H 80 N CF₂HCF₂CH₂ H H

H H 81 N CF₃CF₂CF₂CH₂ H H

H H 82 N CF₃CFHCF₂CH₂ H H

H H

TABLE 14 Present compound A¹ R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² 83 N CF₂HCH₂H H

H H 84 N CF₃CF₂CH₂ H H

H H 85 N CF₂HCF₂CH₂ H H

H H 86 N CF₃CF₂CF₂CH₂ H H

H H 87 N CF₃CFHCF₂CH₂ H H

H H 88 N CF₂HCH₂ H H

H H 89 N CF₃CF₂CH₂ H H

H H 90 N CF₂HCF₂CH₂ H H

H H 91 N CF₃CF₂CF₂CH₂ H H

H H 92 N CF₃CFHCF₂CH₂ H H

H H

TABLE 15 Present compound A¹ R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² 93 N CF₂HCH₂H H

H H 94 N CF₃CF₂CH₂ H H

H H 95 N CF₂HCF₂CH₂ H H

H H 96 N CF₃CF₂CF₂CH₂ H H

H H 97 N CF₃CFHCF₂CH₂ H H

H H 98 N CF₂HCH₂ H H

H H 99 N CF₃CF₂CH₂ H H

H H 100 N CF₂HCF₂CH₂ H H

H H 101 N CF₃CF₂CF₂CH₂ H H

H H 102 N CF₃CFHCF₂CH₂ H H

H H

TABLE 16 Present Compound A¹ R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² 103 N CF₂HCH₂H H

H H 104 N CF₃CF₂CH₂ H H

H H 105 N CF₂HCF₂CH₂ H H

H H 106 N CF₃CF₂CF₂CH₂ H H

H H 107 N CF₃CFHCF₂CH₂ H H

H H 108 N CF₂HCH₂ H H

H H 109 N CF₃CF₂CH₂ H H

H H 110 N CF₂HCF₂CH₂ H H

H H 111 N CF₃CF₂CF₂CH₂ H H

H H 112 N CF₃CFHCF₂CH₂ H H

H H

TABLE 17 Present compound A¹ R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² 113 N CF₂HCH₂H H

H H 114 N CF₃CF₂CH₂ H H

H H 115 N CF₂HCF₂CH₂ H H

H H 116 N CF₃CF₂CF₂CH₂ H H

H H 117 N CF₃CFHCF₂CH₂ H H

H H 118 N CF₂HCH₂ H H

H H 119 N CF₃CF₂CH₂ H H

H H 120 N CF₂HCF₂CH₂ H H

H H 121 N CF₃CF₂CF₂CH₂ H H

H H 122 N CF₃CFHCF₂CH₂ H H

H H

TABLE 18 Present compound A¹ R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² 123 N CF₂HCH₂H H

H H 124 N CF₃CF₂CH₂ H H

H H 125 N CF₂HCF₂CH₂ H H

H H 126 N CF₃CF₂CF₂CH₂ H H

H H 127 N CF₃CFHCF₂CH₂ H H

H H 128 N CF₂HCH₂ H H

H H 129 N CF₃CF₂CH₂ H H

H H 130 N CF₂HCF₂CH₂ H H

H H 131 N CF₃CF₂CF₂CH₂ H H

H H 132 N CF₃CFHCF₂CH₂ H H

H H

TABLE 19 Present compound A¹ R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² 133 N CF₂HCH₂H

H H H 134 N CF₃CF₂CH₂ H

H H H 135 N CF₂HCF₂CH₂ H

H H H 136 N CF₃CF₂CF₂CH₂ H

H H H 137 N CF₃CFHCF₂CH₂ H

H H H 138 N CF₂HCH₂ H

H H H 139 N CF₃CF₂CH₂ H

H H H 140 N CF₂HCF₂CH₂ H

H H H 141 N CF₃CF₂CF₂CH₂ H

H H H 142 N CF₃CFHCF₂CH₂ H

H H H

TABLE 20 Present compound A¹ R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² 143 N CF₂HCH₂H

H H H 144 N CF₃CF₂CH₂ H

H H H 145 N CF₂HCF₂CH₂ H

H H H 146 N CF₃CF₂CF₂CH₂ H

H H H 147 N CF₃CFHCF₂CH₂ H

H H H 148 N CF₂HCH₂ H

H H H 149 N CF₃CF₂CH₂ H

H H H 150 N CF₂HCF₂CH₂ H

H H H 151 N CF₃CF₂CF₂CH₂ H

H H H 152 N CF₃CFHCF₂CH₂ H

H H H

TABLE 21 Present compound A¹ R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² 153 N CF₂HCH₂H

H H H 154 N CF₃CF₂CH₂ H

H H H 155 N CF₂HCF₂CH₂ H

H H H 156 N CF₃CF₂CF₂CH₂ H

H H H 157 N CF₃CFHCF₂CH₂ H

H H H 158 N CF₂HCH₂ H

H H H 159 N CF₃CF₂CH₂ H

H H H 160 N CF₂HCF₂CH₂ H

H H H 161 N CF₃CF₂CF₂CH₂ H

H H H 162 N CF₃CFHCF₂CH₂ H

H H H

TABLE 22 Present compound A¹ R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² 163 N CF₂HCH₂H

H H H 164 N CF₃CF₂CH₂ H

H H H 165 N CF₂HCF₂CH₂ H

H H H 166 N CF₃CF₂CF₂CH₂ H

H H H 167 N CF₃CFHCF₂CH₂ H

H H H 168 N CF₂HCH₂ H

H H H 169 N CF₃CF₂CH₂ H

H H H 170 N CF₂HCF₂CH₂ H

H H H 171 N CF₃CF₂CF₂CH₂ H

H H H 172 N CF₃CFHCF₂CH₂ H

H H H

TABLE 23 Present compound A¹ R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² 173 N CF₂HCH₂H

H H H 174 N CF₃CF₂CH₂ H

H H H 175 N CF₂HCF₂CH₂ H

H H H 176 N CF₃CF₂CF₂CH₂ H

H H H 177 N CF₃CFHCF₂CH₂ H

H H H 178 N CF₂HCH₂ H

H H H 179 N CF₃CF₂CH₂ H

H H H 180 N CF₂HCF₂CH₂ H

H H H 181 N CF₃CF₂CF₂CH₂ H

H H H 182 N CF₃CFHCF₂CH₂ H

H H H

TABLE 24 Present compound A¹ R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² 183 N CF₂HCH₂H

H H H 184 N CF₃CF₂CH₂ H

H H H 185 N CF₂HCF₂CH₂ H

H H H 186 N CF₃CF₂CF₂CH₂ H

H H H 187 N CF₃CFHCF₂CH₂ H

H H H 188 N CF₂HCH₂ H

H H H 189 N CF₃CF₂CH₂ H

H H H 190 N CF₂HCF₂CH₂ H

H H H 191 N CF₃CF₂CF₂CH₂ H

H H H 192 N CF₃CFHCF₂CH₂ H

H H H

TABLE 25 Present compound A¹ R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² 193 N CF₂HCH₂H

H H H 194 N CF₃CF₂CH₂ H

H H H 195 N CF₂HCF₂CH₂ H

H H H 196 N CF₃CF₂CF₂CH₂ H

H H H 197 N CF₃CFHCF₂CH₂ H

H H H 198 N CF₂HCH₂ H H H H 199 N CF₃CF₂CH₂ H H H H 200 N CF₂HCF₂CH₂ H HH H 201 N CF₃CF₂CF₂CH₂ H H H H 202 N CF₃CFHCF₂CH₂ H H H H

TABLE 26 Present compound A¹ R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² 203 N CF₂HCH₂H

H H H 204 N CF₃CF₂CH₂ H

H H H 205 N CF₂HCF₂CH₂ H

H H H 206 N CF₃CF₂CF₂CH₂ H

H H H 207 N CF₃CFHCF₂CH₂ H

H H H 208 N CF₂HCH₂ H

H H H 209 N CF₃CF₂CH₂ H

H H H 210 N CF₂HCF₂CH₂ H

H H H 211 N CF₃CF₂CF₂CH₂ H

H H H 212 N CF₃CFHCF₂CH₂ H

H H H

TABLE 27 Present compound A¹ R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² 213 N CF₂HCH₂H

H H H 214 N CF₃CF₂CH₂ H

H H H 215 N CF₂HCF₂CH₂ H

H H H 216 N CF₃CF₂CF₂CH₂ H

H H H 217 N CF₃CFHCF₂CH₂ H

H H H 218 N CF₂HCH₂ H

H H H 219 N CF₃CF₂CH₂ H

H H H 220 N CF₂HCF₂CH₂ H

H H H 221 N CF₃CF₂CF₂CH₂ H

H H H 222 N CF₃CFHCF₂CH₂ H

H H H

TABLE 28 Present compound A¹ R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² 223 N CF₂HCH₂H

H H H 224 N CF₃CF₂CH₂ H

H H H 225 N CF₂HCF₂CH₂ H

H H H 226 N CF₃CF₂CF₂CH₂ H

H H H 227 N CF₃CFHCF₂CH₂ H

H H H 228 N CF₂HCH₂ H

H H H 229 N CF₃CF₂CH₂ H

H H H 230 N CF₂HCF₂CH₂ H

H H H 231 N CF₃CF₂CF₂CH₂ H

H H H 232 N CF₃CFHCF₂CH₂ H

H H H

TABLE 29 Present compound A¹ R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² 233 N CF₂HCH₂H

H H H 234 N CF₃CF₂CH₂ H

H H H 235 N CF₂HCF₂CH₂ H

H H H 236 N CF₃CF₂CF₂CH₂ H

H H H 237 N CF₃CFHCF₂CH₂ H

H H H 238 N CF₂HCH₂ H

H H H 239 N CF₃CF₂CH₂ H

H H H 240 N CF₂HCF₂CH₂ H

H H H 241 N CF₃CF₂CF₂CH₂ H

H H H 242 N CF₃CFHCF₂CH₂ H

H H H

TABLE 30 Present compound A¹ R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² 243 N CF₂HCH₂H

H H H 244 N CF₃CF₂CH₂ H

H H H 245 N CF₂HCF₂CH₂ H

H H H 246 N CF₃CF₂CF₂CH₂ H

H H H 247 N CF₃CFHCF₂CH₂ H

H H H 248 N CF₂HCH₂ H

H H H 249 N CF₃CF₂CH₂ H

H H H 250 N CF₂HCF₂CH₂ H

H H H 251 N CF₃CF₂CF₂CH₂ H

H H H 252 N CF₃CFHCF₂CH₂ H

H H H

TABLE 31 Present compound A¹ R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² 253 N CF₂HCH₂H

H H H 254 N CF₃CF₂CH₂ H

H H H 255 N CF₂HCF₂CH₂ H

H H H 256 N CF₃CF₂CF₂CH₂ H

H H H 257 N CF₃CFHCF₂CH₂ H

H H H 258 N CF₂HCH₂ H

H H H 259 N CF₃CF₂CH₂ H

H H H 260 N CF₂HCF₂CH₂ H

H H H 261 N CF₃CF₂CF₂CH₂ H

H H H 262 N CF₃CFHCF₂CH₂ H

H H H

TABLE 32 Present compound A¹ R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² 263 N CF₂HCH₂H

H H H 264 N CF₃CF₂CH₂ H

H H H 265 N CF₂HCF₂CH₂ H

H H H 266 N CF₃CF₂CF₂CH₂ H

H H H 267 N CF₃CFHCF₂CH₂ H

H H H

TABLE 33 Present compound A¹ R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² 268 N CF₂HCH₂H OCH₃ H H H 269 N CF₃CF₂CH₂ H OCH₃ H H H 270 N CF₂HCF₂CH₂ H OCH₃ H H H271 N CF₃CF₂CF₂CH₂ H OCH₃ H H H 272 N CF₃CFHCF₂CH₂ H OCH₃ H H H 273 NCF₂HCH₂ H OCH₂CH₃ H H H 274 N CF₃CF₂CH₂ H OCH₂CH₃ H H H 275 N CF₂HCF₂CH₂H OCH₂CH₃ H H H 276 N CF₃CF₂CF₂CH₂ H OCH₂CH₃ H H H 277 N CF₃CFHCF₂CH₂ HOCH₂CH₃ H H H 278 N CF₂HCH₂ H OCH (CH₃)₂ H H H 279 N CF₃CF₂CH₂ H OCH(CH₃)₂ H H H 280 N CF₂HCF₂CH₂ H OCH (CH₃)₂ H H H 281 N CF₃CF₂CF₂CH₂ HOCH (CH₃)₂ H H H 282 N CF₃CFHCF₂CH₂ H OCH (CH₃)₂ H H H 283 N CF₂HCH₂ HOCH₂CH₂N (CH₃)₂ H H H 284 N CF₃CF₂CH₂ H OCH₂CH₂N (CH₃)₂ H H H 285 NCF₂HCF₂CH₂ H OCH₂CH₂N (CH₃)₂ H H H 286 N CF₃CF₂CF₂CH₂ H OCH₂CH₂N (CH₃)₂H H H 287 N CF₃CFHCF₂CH₂ H OCH₂CH₂N (CH₃)₂ H H H 288 N CF₂HCH₂ H OCH₂CF₃H H H 289 N CF₃CF₂CH₂ H OCH₂CF₃ H H H 290 N CF₂HCF₂CH₂ H OCH₂CF₃ H H H291 N CF₃CF₂CF₂CH₂ H OCH₂CF₃ H H H 292 N CF₃CFHCF₂CH₂ H OCH₂CF₃ H H H

TABLE 34 Present compound A¹ R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² 293 N CF₂HCH₂H OCH₂CF₃ H H H 294 N CF₃CF₂CH₂ H OCH₂CF₃ H H H 295 N CF₂HCF₂CH₂ HOCH₂CF₃ H H H 296 N CF₃CF₂CF₂CH₂ H OCH₂CF₃ H H H 297 N CF₃CFHCF₂CH₂ HOCH₂CF₃ H H H 298 N CF₂HCH₂ H OCH₂CF₂CF₂H H H H 299 N CF₃CF₂CH₂ HOCH₂CF₂CF₂H H H H 300 N CF₂HCF₂CH₂ H OCH₂CF₂CF₂H H H H 301 NCF₃CF₂CF₂CH₂ H OCH₂CF₂CF₂H H H H 302 N CF₃CFHCF₂CH₂ H OCH₂CF₂CF₂H H H H303 N CF₂HCH₂ H OCH₂CF₂CF₃ H H H 304 N CF₃CF₂CH₂ H OCH₂CF₂CF₃ H H H 305N CF₂HCF₂CH₂ H OCH₂CF₂CF₃ H H H 306 N CF₃CF₂CF₂CH₂ H OCH₂CF₂CF₃ H H H307 N CF₃CFHCF₂CH₂ H OCH₂CF₂CF₃ H H H 308 N CF₂HCH₂ H NHC (O) CH₃ H H H309 N CF₃CF₂CH₂ H NHC (O) CH₃ H H H 310 N CF₂HCF₂CH₂ H NHC (O) CH₃ H H H311 N CF₃CF₂CF₂CH₂ H NHC (O) CH₃ H H H 312 N CF₃CFHCF₂CH₂ H NHC (O) CH₃H H H 313 N CF₂HCH₂ H NHC (O) CH₂CH₃ H H H 314 N CF₃CF₂CH₂ H NHC (O)CH₂CH₃ H H H 315 N CF₂HCF₂CH₂ H NHC (O) CH₂CH₃ H H H 316 N CF₃CF₂CF₂CH₂H NHC (O) CH₂CH₃ H H H 317 N CF₃CFHCF₂CH₂ H NHC (O) CH₂CH₃ H H H

TABLE 35 Present compound A¹ R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² 318 N CF₂HCH₂H

H H H 319 N CF₃CF₂CH₂ H

H H H 320 N CF₂HCF₂CH₂ H

H H H 321 N CF₃CF₂CF₂CH₂ H

H H H 322 N CF₃CFHCF₂CH₂ H

H H H 323 N CF₂HCH₂ H

H H H 324 N CF₃CF₂CH₂ H

H H H 325 N CF₂HCF₂CH₂ H

H H H 326 N CF₃CF₂CF₂CH₂ H

H H H 327 N CF₃CFHCF₂CH₂ H

H H H

TABLE 36 Present compound A¹ R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² 328 N CF₂HCH₂H NHC (O) OCH₃ H H H 329 N CF₃CF₂CH₂ H NHC (O) OCH₃ H H H 330 NCF₂HCF₂CH₂ H NHC (O) OCH₃ H H H 331 N CF₃CF₂CF₂CH₂ H NHC (O) OCH₃ H H H332 N CF₃CFHCF₂CH₂ H NHC (O) OCH₃ H H H 333 N CF₂HCH₂ H NHC (O) OCH₂CH₃H H H 334 N CF₃CF₂CH₂ H NHC (O) OCH₂CH₃ H H H 335 N CF₂HCF₂CH₂ H NHC (O)OCH₂CH₃ H H H 336 N CF₃CF₂CF₂CH₂ H NHC (O) OCH₂CH₃ H H H 337 NCF₃CFHCF₂CH₂ H NHC (O) OCH₂CH₃ H H H 338 N CF₂HCH₂ H OCH₂CH₂CH₃ H H H339 N CF₃CF₂CH₂ H OCH₂CH₂CH₃ H H H 340 N CF₂HCF₂CH₂ H OCH₂CH₂CH₃ H H H341 N CF₃CF₂CF₂CH₂ H OCH₂CH₂CH₃ H H H 342 N CF₃CFHCF₂CH₂ H OCH₂CH₂CH₃ HH H

A compound represented by formula (M-100)

[wherein, R³⁰¹, R³⁰², R³⁰³, R⁶⁰¹, R⁶⁰², R¹⁰⁰, A¹, and V represent anycombination indicated in the Table 37 below.]can be prepared according to the processes described above.

TABLE 37 Intermediate compound A¹ V R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ r⁶⁰¹ R⁶⁰² a-1 NF CF₃CH₂ H H H H H a-2 N F CF₂HCH₂ H H H H H a-3 N F CF₃CF₂CH₂ H H H H Ha-4 N F CF₂HCF₂CH₂ H H H H H a-5 N F CF₃CF₂CF₂CH₂ H H H H H a-6 N FCF₃CFHCF₂CH₂ H H H H H a-7 N F CF₂HCF₂CF₂CF₂CH₂ H H H H H a-8 N ClCF₃CH₂ H CF₃ H H H a-9 N Cl CF₂HCH₂ H CF₃ H H H a-10 N Cl CF₃CF₂CH₂ HCF₃ H H H a-11 N Cl CF₂HCF₂CH₂ H CF₃ H H H a-12 N Cl CF₃CF₂CF₂CH₂ H CF₃H H H a-13 N Cl CF₃CFHCF₂CH₂ H CF₃ H H H a-14 N Cl CF₂HCF₂CF₂CF₂CH₂ HCF₃ H H H a-15 CH F CF₃CH₂ H CF₃ H H H a-16 CH F CF₂HCH₂ H CF₃ H H Ha-17 CH F CF₃CF₂CH₂ H CF₃ H H H a-18 CH F CF₂HCF₂CH₂ H CF₃ H H H a-19 CHF CF₃CF₂CF₂CH₂ H CF₃ H H H a-20 CH F CF₃CFHCF₂CH₂ H CF₃ H H H a-21 CH FCF₂HCF₂CF₂CF₂CH₂ H CF₃ H H H

A compound represented by formula (M-200)

[wherein, R³⁰¹, R³⁰², R³⁰³, R⁶⁰¹, R⁶⁰², R¹⁰⁰, and A¹ represent anycombination indicated in the Table 38 below.]can be prepared according to the processes described above.

TABLE 38 Inter- mediate com- pound A¹ R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² b-1N CF₃CH₂ H H H H H b-2 N CF₂HCH₂ H H H H H b-3 N CF₃CF₂CH₂ H H H H H b-4N CF₂HCF₂CH₂ H H H H H b-5 N CF₃CF₂CF₂CH₂ H H H H H b-6 N CF₃CFHCF₂CH₂ HH H H H b-7 N CF₂HCF₂CF₂CF₂CH₂ H H H H H b-8 N CF₃CH₂ H CF₃ H H H b-9 NCF₂HCH₂ H CF₃ H H H b-10 N CF₃CF₂CH₂ H CF₃ H H H b-11 N CF₂HCF₂CH₂ H CF₃H H H b-12 N CF₃CF₂CF₂CH₂ H CF₃ H H H b-13 N CF₃CFHCF₂CH₂ H CF₃ H H Hb-14 N CF₂HCF₂CF₂CF₂CH₂ H CF₃ H H H b-15 CH CF₃CH₂ H CF₃ H H H b-16 CHCF₂HCH₂ H CF₃ H H H b-17 CH CF₃CF₂CH₂ H CF₃ H H H b-18 CH CF₂HCF₂CH₂ HCF₃ H H H b-19 CH CF₃CF₂CF₂CH₂ H CF₃ H H H b-20 CH CF₃CFHCF₂CH₂ H CF₃ HH H b-21 CH CF₂HCF₂CF₂CF₂CH₂ H CF₃ H H H

A compound represented by formula (M300)

[wherein, R³⁰¹, R³⁰², R³⁰³, R⁶⁰¹, R⁶⁰², R¹⁰⁰, and A¹ represent anycombination indicated in the Table 39 below.]can be prepared according to the processes described above.

TABLE 39 Intermediate compound A¹ R²⁰⁰ n R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² c-1 NCH₃ 2 H H H H H c-2 N CH₃CH₂ 2 H H H H H c-3 N CH₃CH₂CH₂ 2 H H H H H c-4N CH(CH₃)₂ 2 H H H H H c-5 N CF₃CH₂ 2 H H H H H c-6 N

2 H H H H H c-7 N

2 H H H H H c-8 N CH₃ 2 H CF₃ H H H c-9 N CH₃CH₂ 2 H CF₃ H H H c-10 NCH₃CH₂CH₂ 2 H CF₃ H H H c-11 N CH(CH₃)₂ 2 H CF₃ H H H c-12 N CF₃CH₂ 2 HCF₃ H H H c-13 N

2 H CF₃ H H H c-14 N

2 H CF₃ H H H c-15 CH CH₃ 2 H CF₃ H H H c-16 CH CH₃CH₂ 2 H CF₃ H H Hc-17 CH CH₃CH₂CH₂ 2 H CF₃ H H H c-18 CH CH(CH₃)₂ 2 H CF₃ H H H c-19 CHCF₃CH₂ 2 H CF₃ H H H c-20 CH

2 H CF₃ H H H c-21 CH

2 H CF₃ H H H

A compound represented by formula (M400)

[wherein, R³⁰¹, R³⁰², R³⁰³, R⁶⁰¹, R⁶⁰², R²⁰⁰, V and A¹ represent anycombination indicated in the Table 40 below.]can be prepared according to the processes described above.

TABLE 40 Inter- mediate com- pound A¹ V R²⁰⁰ n R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰²d-1 N Cl CH₃ 2 H H H H H d-2 N Cl CH₃CH₂ 2 H H H H H d-3 N Cl CH₃CH₂CH₂2 H H H H H d-4 N Cl CH(CH₃)₂ 2 H H H H H d-5 N Cl CF₃CH₂ 2 H H H H Hd-6 N Cl

2 H H H H H d-7 N Cl

2 H H H H H d-8 N Cl CH₃ 2 H CF₃ H H H d-9 N Cl CH₃CH₂ 2 H CF₃ H H Hd-10 N Cl CH₃CH₂CH₂ 2 H CF₃ H H H d-11 N Cl CH(CH₃)₂ 2 H CF₃ H H H d-12N Cl CF₃CH₂ 2 H CF₃ H H H d-13 N Cl

2 H CF₃ H H H d-14 N Cl

2 H CF₃ H H H d-15 CH Cl CH₃ 2 H CF₃ H H H d-16 CH Cl CH₃CH₂ 2 H CF₃ H HH d-17 CH Cl CH₃CH₂CH₂ 2 H CF₃ H H H d-18 CH Cl CH(CH₃)₂ 2 H CF₃ H H Hd-19 CH Cl CF₃CH₂ 2 H CF₃ H H H d-20 CH Cl

2 H CF₃ H H H d-21 CH Cl

2 H CF₃ H H H

A compound represented by formula (M330)

[wherein, R⁶⁰¹, R⁶⁰², R²⁰⁰ and R⁴⁰⁰ represent any combination indicatedin the Table 41 to Table 43 below.]can be prepared according to the processes described above.

TABLE 41 Intermediate compound R⁴⁰⁰ R²⁰⁰ n R⁶⁰¹ R⁶⁰² e-1 F CH₃ 2 H H e-2Cl CH₃ 2 H H e-3 Br CH₃ 2 H H e-4 CH₃O CH₃ 2 H H e-5 CH₃CH₂O CH₃ 2 H He-6 CF₃CH(CH₃) CH₃ 2 H H e-7 CF₃CF₂CH(CH₃) CH₃ 2 H H e-8 CF₃CH₂ CH₃ 2 HH e-9 CF₂HCH₂ CH₃ 2 H H e-10 CF₃CF₂CH₂ CH₃ 2 H H e-11 CF₂HCF₂CH₂ CH₃ 2 HH e-12 CF₃CF₂CF₂CH₂ CH₃ 2 H H e-13 CF₃CFHCF₂CH₂ CH₃ 2 H H e-14CF₂HCF₂CF₂CF₂CH₂ CH₃ 2 H H e-15 F CH₃CH₂ 2 H H e-16 Cl CH₃CH₂ 2 H H e-17Br CH₃CH₂ 2 H H e-18 CH₃O CH₃CH₂ 2 H H e-19 CH₃CH₂O CH₃CH₂ 2 H H e-20CF₃CH(CH₃) CH₃CH₂ 2 H H e-21 CF₃CF₂CH(CH₃) CH₃CH₂ 2 H H e-22 CF₃CH₂CH₃CH₂ 2 H H e-23 CF₂HCH₂ CH₃CH₂ 2 H H e-24 CF₃CF₂CH₂ CH₃CH₂ 2 H H e-25CF₂HCF₂CH₂ CH₃CH₂ 2 H H e-26 CF₃CF₂CF₂CH₂ CH₃CH₂ 2 H H e-27 CF₃CFHCF₂CH₂CH₃CH₂ 2 H H e-28 CF₂HCF₂CF₂CF₂CH₂ CH₃CH₂ 2 H H

TABLE 42 Intermediate compound R⁴⁰⁰ R²⁰⁰ n R⁶⁰¹ R⁶⁰² e-29 F

2 H H e-30 Cl

2 H H e-31 Br

2 H H e-32 CH₃O

2 H H e-33 CH₃CH₂O

2 H H e-34 CF₃CH(CH₃)

2 H H e-35 CF₃CF₂CH(CH₃)

2 H H e-36 CF₃CH₂

2 H H e-37 CF₂HCH₂

2 H H e-38 CF₃CF₂CH₂

2 H H e-39 CF₂HCF₂CH₂

2 H H e-40 CF₃CF₂CF₂CH₂

2 H H e-41 CF₃CFHCF₂CH₂

2 H H e-42 CF₂HCF₂CF₂CF₂CH₂

2 H HTable 43

TABLE 43 Intermediate compound R⁴⁰⁰ R²⁰⁰ n R⁶⁰¹ R⁶⁰² e-43 F

2 H H e-44 Cl

2 H H e-45 Br

2 H H e-46 CH₃O

2 H H e-47 CH₃CH₂O

2 H H e-48 CF₃CH(CH₃)

2 H H e-49 CF₃CF₂CH(CH₃)

2 H H e-50 CF₃CH₂

2 H H e-51 CF₂HCH₂

2 H H e-52 CF₃CF₂CH₂

2 H H e-53 CF₂HCF₂CH₂

2 H H e-54 CF₃CF₂CF₂CH₂

2 H H e-55 CF₃CFHCF₂CH₂

2 H H e-56 CF₂HCF₂CF₂CF₂CH₂

2 H H

A compound represented by formula (M331)

[wherein, R⁶⁰¹, R⁶⁰², R²⁰⁰ and R⁴⁰⁰ represent any combination indicatedin the Table 44 to Table 46 below.]can be prepared according to the processes described above.

TABLE 44 Intermediate compound R⁴⁰⁰ R²⁰⁰ n R⁶⁰¹ R⁶⁰² f-1 F CH₃ 2 H H f-2Cl CH₃ 2 H H f-3 Br CH₃ 2 H H f-4 CH₃O CH₃ 2 H H f-5 CH₃CH₂O CH₃ 2 H Hf-6 CF₃CH(CH₃) CH₃ 2 H H f-7 CF₃CF₂CH(CH₃) CH₃ 2 H H f-8 CF₃CH₂ CH₃ 2 HH f-9 CF₂HCH₂ CH₃ 2 H H f-10 CF₃CF₂CH₂ CH₃ 2 H H f-11 CF₂HCF₂CH₂ CH₃ 2 HH f-12 CF₃CF₂CF₂CH₂ CH₃ 2 H H f-13 CF₃CFHCF₂CH₂ CH₃ 2 H H f-14CF₂HCF₂CF₂CF₂CH₂ CH₃ 2 H H f-15 F CH₃CH₂ 2 H H f-16 Cl CH₃CH₂ 2 H H f-17Br CH₃CH₂ 2 H H f-18 CH₃O CH₃CH₂ 2 H H f-19 CH₃CH₂O CH₃CH₂ 2 H H f-20CF₃CH(CH₃) CH₃CH₂ 2 H H f-21 CF₃CF₂CH(CH₃) CH₃CH₂ 2 H H f-22 CF₃CH₂CH₃CH₂ 2 H H f-23 CF₂HCH₂ CH₃CH₂ 2 H H f-24 CF₃CF₂CH₂ CH₃CH₂ 2 H H f-25CF₂HCF₂CH₂ CH₃CH₂ 2 H H f-26 CF₃CF₂CF₂CH₂ CH₃CH₂ 2 H H f-27 CF₃CFHCF₂CH₂CH₃CH₂ 2 H H f-28 CF₂HCF₂CF₂CF₂CH₂ CH₃CH₂ 2 H H

TABLE 45 Intermediate compound R⁴⁰⁰ R²⁰⁰ n R⁶⁰¹ R⁶⁰² f-29 F

2 H H f-30 Cl

2 H H f-31 Br

2 H H f-32 CH₃O

2 H H f-33 CH₃CH₂O

2 H H f-34 CF₃CH(CH₃)

2 H H f-35 CF₃CF₂CH(CH₃)

2 H H f-36 CF₃CH₂

2 H H f-37 CF₂HCH₂

2 H H f-38 CF₃CF₂CH₂

2 H H f-39 CF₂HCF₂CH₂

2 H H f-40 CF₃CF₂CF₂CH₂

2 H H f-41 CF₃CFHCF₂CH₂

2 H H f-42 CF₂HCF₂CF₂CF₂CH₂

2 H H

TABLE 46 Intermediate compound R⁴⁰⁰ R²⁰⁰ n R⁶⁰¹ R⁶⁰² f-43 F

2 H H f-44 Cl

2 H H f-45 Br

2 H H f-46 CH₃O

2 H H f-47 CH₃CH₂O

2 H H f-48 CF₃CH(CH₃)

2 H H f-49 CF₃CF₂CH(CH₃)

2 H H f-50 CF₃CH₂

2 H H f-51 CF₂HCH₂

2 H H f-52 CF₃CF₂CH₂

2 H H f-53 CF₂HCF₂CH₂

2 H H f-54 CF₃CF₂CF₂CH₂

2 H H f-55 CF₃CFHCF₂CH₂

2 H H f-56 CF₂HCF₂CF₂CF₂CH₂

2 H H

Next, the formulation examples of the Present compound are shown below.The “parts” represents “part by weight” unless otherwise specified.

Formulation Example 1

Into a mixture of 35 parts of xylene and 35 parts of DMF, 10 parts ofeach of the Present compounds 1 to 348 is dissolved, and then 14 partsof polyoxyethylene styryl phenyl ether and 6 parts of calciumdodecylbenzene sulfonate are added, followed by mixing them to obtaineach formulation.

Formulation Example 2

Four (4) parts of sodium lauryl sulfate, 2 parts of calcium ligninsulfonate, 20 parts of synthetic hydrated silicon oxide fine powder and54 parts of diatomaceous earth are mixed, and further 20 parts of eachof the Present compounds 1 to 348 is added, followed by mixing them toobtain each wettable powders.

Formulation Example 3

To 2 parts of each of the Present compounds 1 to 348, 1 part ofsynthetic hydrated silicon oxide fine powder, 2 parts of calcium ligninsulfonate, 30 parts of bentonite and 65 parts of kaolin clay are added,followed by mixing, granulation with a granulator and forced-air dryingto obtain each granular formulation.

Formulation Example 4

Into an appropriate amount of acetone, 1 part of each the Presentcompounds 1 to 348 is mixed, and then 5 parts of synthetic hydroussilicon oxide fine powder, 0.3 parts of isopropyl acid phosphate and93.7 parts of kaolin clay are added, followed by mixing with stirringthoroughly and removal of acetone from the mixture by evaporation toobtain each of powder formulation.

Formulation Example 5

A mixture of 35 parts of polyoxyethylene alkyl ether sulfate ammoniumsalt and white carbon (weight ratio of 1:1), 10 parts of each of thePresent compounds 1 to 348, and 55 parts of water are mixed, followed byfinely grounding by a wet grinding method to obtain each flowableformulation.

Formulation Example 6

Into a mixture of 5 parts of xylene and 5 parts of trichloroethane, 0.1parts of each of the Present compounds 1 to 348 is dissolved, and theresulting mixture is then mixed with 89.9 parts of kerosene to obtaineach oil solution.

Formulation Example 7

Into 0.5 mL of acetone, 10 mg of each of the Present compounds 1 to 348is dissolved and the solution is added dropwise to 5 g of a solid feedpowder for an animal (solid feed powder for rearing and breeding CE-2,manufactured by CLEA Japan, Inc.), followed by mixing the resultingmixture uniformly, and then by drying them by evaporation of acetone toobtain each poison bait.

Formulation Example 8

Into an aerosol can, 0.1 part of each of the Present compound 1 to 348and 49.9 parts of Neothiozole (Chuo Kasei Co., Ltd.) are placed. Aftermounting an aerosol valve, 25 parts of dimethylether and 25 parts of LPGare filled, followed by shaking and further mounting an actuator toobtain an oily aerosol.

Formulation Example 9

A mixture of 0.6 part of each of the Present compounds to 348, 0.01 partof BHT (2,6-di-tert-butyl-4-methylphenol), 5 parts of xylene, 3.39 partsof deodorized kerosine and 1 part of an emulsifier {Rheodol MO-60(registered trademark of Kao Corporation)} and 50 parts of distilledwater are filled into an aerosol container, and a valve part isattached. Then, 40 parts of a propellant (LPG) is filled therein throughthe valve under pressure to obtain an aqueous aerosol.

Formulation Example 10

Zero point one (0.1) parts of each of the Present compounds 1 to 348 aremixed into 2 mL of propylene glycol, and the resulting solution isimpregnated into a ceramic plate having a size of 4.0 cm×4.0 cm and athickness of 1.2 cm, to obtain thermal fumigants.

Formulation Example 11

Five (5) parts of each of the Present compounds 1 to 348, and 95 partsof ethylene-methyl methacrylate copolymer (the ratio of the methylmethacrylate in the copolymer: 10 weight %), Acryft (registered bytrademark) WD 301, manufactured by Sumitomo Chemical Co. Ltd.) aremelted and kneaded with a closed type pressure kneader, and theresulting kneaded product is extruded from an extrusion molding machinethrough a molding die to obtain a rod-shaped molded product having alength of 15 cm and a diameter of 3 mm.

Formulation Example 12

Five (5) parts of each of the Present compounds 1 to 348, and 95 partsof plasticized polyvinyl chloride resin are melted and kneaded with aclosed type pressure kneader, and the resulting kneaded product isextruded from an extrusion molding machine through a molding die toobtain a rod-shaped molded product having a length of 15 cm and adiameter of 3 mm.

Formulation Example 13

One hundred (100) mg of each of the Present compounds 1 to 348, 68.75 mgof lactose, 237.5 mg of corn starch, 43.75 mg of microcrystallinecellulose, 18.75 mg of polyvinylpyrrolidone, 28.75 mg of sodiumcarbomethyl starch and 25 mg of magnesium stearate are mixed, and theresulting mixture was compressed to an appropriate size to obtain atablet.

Formulation Example 14

Twenty five (25) mg of each of the Present compounds 1 to 348, 60 mg oflactose, 25 mg of corn starch, 6 mg of carmellose calcium and anappropriate amount of 5% of hydroxypropyl methylcellulose are mixed, andthe resulting mixture are filled into a hard shell gelatin capsule or ahydroxypropyl methylcellulose capsule to obtain capsules.

Formulation Example 15

To 100 mg of each of the Present compounds 1 to 348, 500 mg of fumaricacid, 2000 mg of granulated sugar, 13,000 mg of sorbitol (70% solution),100 mg of Veegum K (manufactured by Vanderbilt Co.), 35 mg of perfumeand 500 mg of coloring agent, a distilled water is added so that a finalvolume is set to be 100 mL, followed by mixing them to obtain asuspension for oral administration.

Formulation Example 16

Into a mixture of 5% by weight of an emulsifier, 3% by weight of benzylalcohol and 30% by weight of propylene glycol, 5% by weight of each ofthe Present compounds 1 to 348 is dissolved, and phosphate buffer isadded thereto so that a pH of the solution is set to be 6.0 to 6.5, andwater is added as the rest parts to obtain the solution for oraladministration.

Formulation Example 17

To a mixture of 57% by weight of fractional distillated palm oil and 3%by weight of polysorbate 85, 5% by weight of aluminum distearate isadded, and heated to disperse it. The resulting mixture is cooled toroom temperature, and 25% by weight of saccharin is dispersed in an oilvehicle. Ten (10) % by weight of each of the Present compounds 1 to 348is divided thereto to obtain a paste for oral administration.

Formulation Example 18

Five (5) % by weight of each of the Present compounds 1 to 348 is mixedwith 95% by weight of limestone filler, followed by a wet granulation ofthe resulting mixture to obtain a granule for oral administration.

Formulation Example 19

Into 80 parts of diethylene glycol monomethyl ether, 5 parts of each ofthe Present compounds 1 to 348 is dissolved, and 15 parts of propylenecarbonate is added thereto, and the resulting mixture is mixed to obtaina spot-on solution.

Formulation Example 20

Into 70 parts of diethylene glycol monomethyl ether, parts of each ofthe Present compounds 1 to 348 is dissolved, and 20 parts of2-octyldodecanol is added thereto, and the resulting mixture is mixed toobtain a pour-on solution.

Formulation Example 21

To 0.5 parts of each of the Present compounds 1 to 348, parts of Nikkol(registered by trademark) TEALS-42 (manufactured by Nikko Chemical Co.Ltd.: 42% of aqueous solution of lauryl sulfuric acid triethanol amine)and 20 parts of propylene glycol are added, and the resulting mixture ismixed with stirring thoroughly, and 19.5 parts of water is then addedthereto and the resulting mixture is further mixed with stirringthoroughly to obtain a hydrogenous solution of shampoo formulation.

Formulation Example 22

Zero point fifteen (0.15)% by weight of each of the Present compounds 1to 348, 95% by weight of animal feed, as well as 4.85% by weight of amixture of dibasic calcium phosphate, diatomaceous earth, aerosol andcarbonate (or chalk) are mixed with stirring thoroughly to obtain apremix for animal feed.

Formulation Example 23

Seven point two (7.2) g of each of the Present compounds 1 to 348, and92.8 g of Hosco (registered trademark) S-55 (manufactured by MaruishiPharmaceuticals) are melted and mixed at 100° C., and the resultingmixture was poured into a suppository mold, followed by performing acooling solidification to obtain a suppository.

Next, Test Examples are used to show an efficacy of the Present compoundon controlling harmful arthropods.

The following test examples were carried out at 25° C.

Test Example 1

The test compounds are made to a formulation according to a similarmethod to that described in the Formulation Example 5, and thereto isadded water containing 0.03 v/v % of a spreader to prepare a dilutedsolution containing a prescribed concentration of the test compound.

Cucumber (Cucumis sativus) seedling (on the developmental stage of thesecond true leaf) is planted in a polyethylene cup and approximately 30heads of cotton aphid (Aphis gossypii) (all stages of life) are releasedonto the leaves of the cucumber. After 1 day, the diluted solutions aresprayed into the seedling in a ratio of 10 mL/seedling. After 5 days,the number of the surviving insects was examined and the controllingvalue was calculated by the following equation.Controlling value (%)={1−(Cb×Tai)/(Cai×Tb)}×100wherein the symbols in the formula represent the following descriptions.

Cb: Number of the test insects in untreated group;

Cai: Number of the surviving insects at the time of the investigation inuntreated group;

Tb: Number of the test insects in treated group;

Tai: Number of the surviving insects at the time of the investigation intreated group;

Here the “untreated group” represents a group where the similartreatment procedure to that of the treated group except not using thetest compound is done.

The results of the test that was done according to the Test example 1are shown below.

When the prescribed concentration was 500 ppm, the treated group thatwas treated with each of the below-mentioned Present compounds showed90% or greater as the controlling value.

Present compound number: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14,15, 16, 18, 19, and 24

The results of the test that was done according to the Test example 1are shown below.

When the prescribed concentration was 200 ppm, the treated group thatwas treated with each of the below-mentioned Present compounds showed90% or greater as the controlling value.

Present compound number: 2, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 16, 18,and 24

Test Example 2

The test compounds are made to a formulation according to a similarmethod to that described in the Formulation Example 5, and thereto isadded water to prepare a diluted solution containing a prescribedconcentration of the test compound.

Cucumber seedling (on the developmental stage of the second true leaf)is planted in a polyethylene cup, and the diluted solutions in the ratioon 5 mL/seedling were irrigated into the plant foot. After 7 days,approximately heads of cotton aphid (all stages of life) were inoculatedonto the cucumber leaves. After additional 6 days, the number of thesurviving insects was examined, and the controlling value was calculatedby the following equation.Controlling value (%)={1−(Cb×Tai)/(Cai×Tb)}×100wherein the symbols in the formula represent the following descriptions.

Cb: Number of the test insects in untreated group;

Cai: Number of the surviving insects at the time of the investigation inuntreated group;

Tb: Number of the test insects in treated group;

Tai: Number of the surviving insects at the time of the investigation intreated group;

Here the “untreated group” represents a group where the similartreatment procedure to that of the treated group except not using thetest compound is done.

The results of the test that was done according to the Test example 2are shown below.

When the prescribed concentration was 200 ppm, the treated group thatwas treated with each of the below-mentioned Present compounds showed90% or greater as the controlling value.

Present compound number: 4, 5, 6, 8, 9, 10, 11, 12, 13, 16, 18, and 24

Test Example 3

The test compounds are made to a formulation according to a similarmethod to that described in the Formulation Example 5, and thereto isadded water containing 0.03 v/v % of a spreader to prepare a dilutedsolution containing a prescribed concentration of the test compound.

Rice (Oryza sativa) seedling (on the developmental stage of the secondtrue leaf) is planted in a polyethylene cup, and the diluted solutionsare sprayed into the seedling in a ratio of 10 mL/seedling. Thereafter,20 heads of 3rd instar larvae of brown planthopper (Nilaparvata lugens)were released onto the rice leaves. After 6 days, the number of thesurviving insects was examined, and the mortality was calculated by thefollowing equation.Mortality (%)={1−the number of the surviving insects/20}×100

The results of the test that was done according to the Test example 3are shown below.

When the prescribed concentration was 500 ppm, each of thebelow-mentioned Present compounds showed 90% or greater as thecontrolling value.

Present compound number: 2, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 16,18, 19, 21, and 24

The results of the test that was done according to the Test example 3are shown below.

When the prescribed concentration was 200 ppm, each of thebelow-mentioned Present compounds showed 90% or greater as thecontrolling value.

Present compound number: 1, 2, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 15, 16,18, and 24

Test Example 4

The test compounds are made to a formulation according to a similarmethod to that described in the Formulation Example 5, and thereto isadded water to prepare a diluted solution containing a prescribedconcentration of the test compound.

The diluted solutions described above were added to the polyethylenecup, and therein was installed Rice seedling (on the developmental stageof the second true leaf) that had been planted in a polyethylene cuphaving a hole in the bottom. After 7 days, 20 heads of 3rd instar larvaeof brown planthopper (Nilaparvata lugens) were released. Afteradditional 6 days, the number of the surviving insects was examined, andthe mortality was calculated by the following equation.Mortality (%)={1−the number of the surviving insects/20}×100

The results of the test that was done according to the Test example 4are shown below.

When the prescribed concentration was 200 ppm, each of thebelow-mentioned Present compounds showed 90% or greater as the mortalityof insects.

Present compound number: 2, 4, 5, 6, 7, 8, 10, 11, 12, 13, 14, 18, and24

Test Example 5

The test compounds are made to a formulation according to a similarmethod to that described in the Formulation Example 5, and thereto isadded water to prepare a diluted solution containing a prescribedconcentration of the test compound.

In the polyethylene cup, 7.7 g of Insecta LF (manufactured by NOSANCORPORATION), an artificial diet was placed, and thereto is irrigated 2mL of the diluted solution. Five (5) heads of fourth instar larvae oftobacco cutworm (Spodoptera litura) are released onto the artificialdiet, and the cup was sealed with a lid. After days, the number of thesurviving tobacco cutworm (Spodoptela litura) was examined, and themortality was calculated by the following equation.Mortality (%)={1−the number of the surviving insects/5}×100

The results of the test that was done according to the Test example 5are shown below.

When the prescribed concentration was 500 ppm, each of thebelow-mentioned Present compounds showed 80% or greater as the mortalityof insects.

Present compound number: 1, 2, 3, 4, 5, 6, 12, 13, 15, and 18

Test Example 6

The test compounds are made to a formulation according to a similarmethod to that described in the Formulation Example 5, and thereto isadded water containing 0.03 v/v % of a spreader to prepare a dilutedsolution containing a prescribed concentration of the test compound.

The diluted solutions are sprayed into the cabbage (Brassicae oleracea)seedling (on the developmental stage of the second to third true leaf)that is planted in the polyethylene cup in a ratio of 20 mL/seedling.Thereafter, the stem and leaf thereof was cut out and then is installedinto the polyethylene cup that is covered with the filter paper. Fiveheads of cabbage moth (Plutella xylostella) at the second instar larvalstages were released into the cup and the cup was covered with the lid.After 5 days, the surviving insects were counted, and the mortality ofinsects was calculated by the following equation.Mortality (%)={1−the number of the surviving insects/5}×100

The results of the test that was done according to the Test example 6are shown below.

When the prescribed concentration was 500 ppm, each of thebelow-mentioned Present compounds showed 80% or greater as the mortalityof insects.

Present compound number: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14,15, 16, 18, 19, 21, and 24

Test Example 7

The test compounds are made to a formulation according to a similarmethod to that described in the Formulation Example 5, and thereto isadded water containing 0.03 v/v % of a spreader to prepare a dilutedsolution containing a prescribed concentration of the test compound. Thediluted solutions are sprayed into the cabbage seedling (on thedevelopmental stage of the third to fourth true leaf) that is planted inthe polyethylene cup in a ratio of 20 mL/seedling. Thereafter, 10 headsof cabbage moth (Plutella xylostella) at the third instar larval stageswere released into the cup, and the insects are held in the polyethylenecup that was covered with a net. After 5 days, the surviving insects arecounted, and the mortality of insects was calculated by the followingequation.Mortality (%)={1−the number of the surviving insects/10}×100

The results of the test that was done according to the Test example 7are shown below.

When the prescribed concentration was 200 ppm, each of thebelow-mentioned Present compounds showed 90% or greater as the mortalityof insects.

Present compound number: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14,15, 16, 18, 19, and 24

Test Example 8

The test compounds are dissolved into a mixed solution ofpolyoxyethylene sorbitan mono-cocoate and acetone (acetone andpolyoxyethylene sorbitan mono-cocoate=5:95 (v/v ratio)) in a ratio of 50μL of the mixed solution per 1 mg of the test compound. Thereto is addedwater containing 0.03% by volume of a spreader to prepare a dilutedsolution containing a prescribed concentration of the test compound.Corns (Zea mays) are sown on a tray overlaid with damped KimWipes(registered trademark). After corns were grown for 5 days, the entireseedling of the corn is immersed into the diluted solution for 30seconds. Thereafter, each two grains of the seedling are installed in aplastic petri dish (90 mm radius), and 10 heads of western corn rootworm(Diabrotica virgifera virgifera) at the second instar larval stages arereleased onto the cup and the cup is covered with a lid. After 5 days,the number of the died insects is counted and the mortality of insectsis calculated by the following equation.Mortality (%)={1−the number of the surviving insects/10}×100

The results of the test that was done according to the Test example 8are shown below.

When the prescribed concentration was 500 ppm, each of thebelow-mentioned Present compounds showed 80% or greater as the mortalityof insects.

Present compound number: 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 14, 16, and 18

Test Example 9

The test compounds are dissolved into a mixed solution of xylene, DMFand surfactants (xylene, DMF and surfactants=4:4:1 (v/v ratio)) in aratio of 10 μL of the mixed solution per 1 mg of the test compound.Thereto is added water containing 0.03% by volume of a spreader toprepare a diluted solution containing a prescribed concentration of thetest compound. The diluted solutions are sprayed into the cucumberseedling (on the developmental stage of the second to third true leaf)that is planted in the polyethylene cup in a ratio of 10 mL/seedling.Thereafter, the second leaf is cut out, and then installed into thepolyethylene cup, and ten heads of cucurbit leaf beetle (Aulacophorafemoralis) at the second instar larval stages were released into the cupand the cup was covered with the lid. After 5 days, the number of diedinsects is counted and the mortality of insects is calculated by thefollowing equation.Mortality of insects (%)=(Number of dead insects/10)×100

The results of the test that was done according to the Test example 9are shown below.

When the prescribed concentration was 50 ppm, each the below-mentionedPresent compounds showed 80% or greater as the mortality of insects.

Present compound number: 2 and 3

Test Example 10

The test compounds are made to a formulation according to a similarmethod to that described in the Formulation Example 5, and thereto isadded water to prepare a diluted solution containing a prescribedconcentration of the test compound.

The bottom of the polyethylene cup having 5.5 cm diameter is matted withthe same size of a filter paper, and 0.7 mL of the diluted solution isadded dropwise to the filter paper, and 30 mg sucrose as bait is placedin the cup uniformly. Ten (10) heads of female adult housefly (Muscadomestica) are released into the polyethylene cup, and the cup wascovered with the lid. After 24 hours, the life and death of housefly isexamined and the number of died insects is counted and the mortality ofinsects is calculated by the following equation.Mortality of insects (%)=(Number of dead insects/Number of testinsects)×100

The results of the test that was done according to the Test example 10are shown below.

When the prescribed concentration was 500 ppm, each the below-mentionedPresent compounds showed 100% as the mortality of insects.

Present compound number: 4, 5, and 6

Next, Test Examples are used to show an efficacy of the presentcomposition on controlling harmful arthropods.

Test Example 11

Each 1 mg of the Present compound is dissolved into a 10 μL of the mixedsolution of xylene, DMF and surfactants (xylene, DMF andsurfactants=4:4:1 (v/v ratio)). Thereto is added water containing 0.02%by volume of a spreader to prepare a diluted solution containing aprescribed concentration of the Present compound.

When the commercially available formulation of the present activeingredient is used, each of the commercially available formulation isdiluted with water containing 0.02 v/v % of the spreader to prepare theprescribed concentration of the diluted solution of the present activeingredient.

Whereas, when the commercially available formulation of the presentactive ingredient is not used, each 1 mg of the present activeingredient is dissolved into a 10 μL of the mixed solution of xylene,DMF and surfactants (xylene, DMF and surfactants=4:4:1 (v/v ratio)).Thereto is added water containing 0.02% by volume of a spreader toprepare a diluted solution containing a prescribed concentration of thepresent active ingredient.

The above prepared diluted solution of the Present compound and theabove prepared diluted solution of the present active ingredient aremixed to prepare the test chemical solution of the compositioncomprising the Present compound and the present active ingredient.

A leaf disk (length 1.5 cm) of the seed leaf of cucumber (Cucumissativus) is placed into each well in a 24 well microplate, and 2wingless adults of a cotton aphid (Aphis gossypii) and 8 nymphs of acotton aphid are released per 1 well, and the test chemical solution issprayed in a ratio of 20 μL per 1 well, which is referred to as atreated group.

Whereas, 20 μL water containing 0.02 v/v % of the spreader is sprayedinto a well instead of the test chemical solution, which is referred toas an untreated group.

After the test chemical solution is dried, the upper part of amicroplate is covered with the gas permeable film sheet (Product Name:AeraSal, manufactured by Excel Scientific Inc.), and 5 days after therelease, the number of the surviving insects of each well is examined.

The controlling value is calculated by the following equation.Controlling value (%)={1−(Tai)/(Cai)}×100wherein the symbols in the formula represent the following descriptions.

Cai: Number of the surviving insects at the time of the investigation inuntreated group;

Tai: Number of the surviving insects at the time of the investigation intreated group;

The composition that is examined according to a method of Test example11 is shown in Table 47. As a result, the composition described in Table47 show an excellent efficacy on controlling harmful arthropods.

TABLE 47 Concentration (ppm) (Present compound + Present activeComposition ingredient) any one kind of Present  200 + 2000 compounds 1to 348 + Clothianidin any one kind of Present 200 + 200 compounds 1 to348 + Clothianidin any one kind of Present 500 + 50  compounds 1 to348 + Clothianidin any one kind of Present  200 + 2000 compounds 1 to348 + Thiamethoxam any one kind of Present 200 + 200 compounds 1 to348 + Thiamethoxam any one kind of Present 500 + 50  compounds 1 to348 + Thiamethoxam any one kind of Present  200 + 2000 compounds 1 to348 + Imidacloprid any one kind of Present 200 + 200 compounds 1 to348 + Imidacloprid any one kind of Present 500 + 50  compounds 1 to348 + Imidacloprid any one kind of Present  200 + 2000 compounds 1 to348 + Thiacloprid any one kind of Present 200 + 200 compounds 1 to 348 +Thiacloprid any one kind of Present 500 + 50  compounds 1 to 348 +Thiacloprid any one kind of Present  200 + 2000 compounds 1 to 348 +Flupyradifurone any one kind of Present 200 + 200 compounds 1 to 348 +Flupyradifurone any one kind of Present 500 + 50  compounds 1 to 348 +Flupyradifurone any one kind of Present  200 + 2000 compounds 1 to 348 +Sulfoxaflor any one kind of Present 200 + 200 compounds 1 to 348 +Sulfoxaflor any one kind of Present 500 + 50  compounds 1 to 348 +Sulfoxaflor any one kind of Present  200 + 2000 compounds 1 to 348 +Triflumezopyrim any one kind of Present 200 + 200 compounds 1 to 348 +Triflumezopyrim any one kind of Present 500 + 50  compounds 1 to 348 +Triflumezopyrim any one kind of Present  200 + 2000 compounds 1 to 348 +Dicloromezotiaz any one kind of Present 200 + 200 compounds 1 to 348 +Dicloromezotiaz any one kind of Present 500 + 50  compounds 1 to 348 +Dicloromezotiaz any one kind of Present  200 + 2000 compounds 1 to 348 +Beta-cyfluthrin any one kind of Present 200 + 200 compounds 1 to 348 +Beta-cyfluthrin any one kind of Present 500 + 50  compounds 1 to 348 +Beta-cyfluthrin any one kind of Present  200 + 2000 compounds 1 to 348 +Tefluthrin any one kind of Present 200 + 200 compounds 1 to 348 +Tefluthrin any one kind of Present 500 + 50  compounds 1 to 348 +Tefluthrin any one kind of Present  200 + 2000 compounds 1 to 348 +Fipronil any one kind of Present 200 + 200 compounds 1 to 348 + Fipronilany one kind of Present 500 + 50  compounds 1 to 348 + Fipronil any onekind of Present  200 + 2000 compounds 1 to 348 + Chlorantraniliprole anyone kind of Present 200 + 200 compounds 1 to 348 + Chlorantraniliproleany one kind of Present 500 + 50  compounds 1 to 348 +Chlorantraniliprole any one kind of Present  200 + 2000 compounds 1 to348 + Cyantraniliprole any one kind of Present 200 + 200 compounds 1 to348 + Cyantraniliprole any one kind of Present 500 + 50  compounds 1 to348 + Cyantraniliprole any one kind of Present  200 + 2000 compounds 1to 348 + Tetraniliprole any one kind of Present 200 + 200 compounds 1 to348 + Tetraniliprole any one kind of Present 500 + 50  compounds 1 to348 + Tetraniliprole any one kind of Present  200 + 2000 compounds 1 to348 + Thiodicarb any one kind of Present 200 + 200 compounds 1 to 348 +Thiodicarb any one kind of Present 500 + 50  compounds 1 to 348 +Thiodicarb any one kind of Present  200 + 2000 compounds 1 to 348 +Carbofuran any one kind of Present 200 + 200 compounds 1 to 348 +Carbofuran any one kind of Present 500 + 50  compounds 1 to 348 +Carbofuran any one kind of Present  200 + 2000 compounds 1 to 348 +fluxametamide any one kind of Present 200 + 200 compounds 1 to 348 +fluxametamide any one kind of Present 500 + 50  compounds 1 to 348 +fluxametamide any one kind of Present  200 + 2000 compounds 1 to 348 +Afoxolaner any one kind of Present 200 + 200 compounds 1 to 348 +Afoxolaner any one kind of Present 500 + 50  compounds 1 to 348 +Afoxolaner any one kind of Present  200 + 2000 compounds 1 to 348 +fluralaner any one kind of Present 200 + 200 compounds 1 to 348 +fluralaner any one kind of Present 500 + 50  compounds 1 to 348 +fluralaner any one kind of Present  200 + 2000 compounds 1 to 348 +broflanilide any one kind of Present 200 + 200 compounds 1 to 348 +broflanilide any one kind of Present 500 + 50  compounds 1 to 348 +broflanilide any one kind of Present  200 + 2000 compounds 1 to 348 +Abamectin any one kind of Present 200 + 200 compounds 1 to 348 +Abamectin any one kind of Present 500 + 5  compounds 1 to 348 +Abamectin any one kind of Present  200 + 2000 compounds 1 to 348 +Fluopyram any one kind of Present 200 + 20  compounds 1 to 348 +Fluopyram any one kind of Present  500 + 0.5  compounds 1 to 348 +Fluopyram any one kind of Present  200 + 2000 compounds 1 to 348 +Fluensulfone any one kind of Present 200 + 200 compounds 1 to 348 +Fluensulfone any one kind of Present 500 + 5  compounds 1 to 348 +Fluensulfone any one kind of Present  200 + 2000 compounds 1 to 348 +Fluazaindolizine any one kind of Present 200 + 200 compounds 1 to 348 +Fluazaindolizine any one kind of Present 500 + 5  compounds 1 to 348 +Fluazaindolizine any one kind of Present  200 + 2000 compounds 1 to348 + Tioxazafen any one kind of Present 200 + 200 compounds 1 to 348 +Tioxazafen any one kind of Present 500 + 5  compounds 1 to 348 +Tioxazafen any one kind of Present  200 + 2000 compounds 1 to 348 +Insecticide compound α1 any one kind of Present 200 + 200 compounds 1 to348 + Insecticide compound α1 any one kind of Present 500 + 50 compounds 1 to 348 + Insecticide compound α1 any one kind of Present 200 + 2000 compounds 1 to 348 + Mycorrhizal fungi any one kind ofPresent 200 + 200 compounds 1 to 348 + Mycorrhizal fungi any one kind ofPresent 500 + 5  compounds 1 to 348 + Mycorrhizal fungi any one kind ofPresent  200 + 2000 compounds 1 to 348 + Bacillus firmus any one kind ofPresent 200 + 200 compounds 1 to 348 + Bacillus firmus any one kind ofPresent 500 + 5  compounds 1 to 348 + Bacillus firmus any one kind ofPresent  200 + 2000 compounds 1 to 348 + Bacillus amyloliquefaciens anyone kind of Present 200 + 200 compounds 1 to 348 + Bacillusamyloliquefaciens any one kind of Present 500 + 5  compounds 1 to 348 +Bacillus amyloliquefaciens any one kind of Present  200 + 2000 compounds1 to 348 + Pasteuria nishizawae any one kind of Present 200 + 200compounds 1 to 348 + Pasteuria nishizawae any one kind of Present 500 +5  compounds 1 to 348 + Pasteuria nishizawae any one kind of Present 200 + 2000 compounds 1 to 348 + Pasteuria penetrans any one kind ofPresent 200 + 200 compounds 1 to 348 + Pasteuria penetrans any one kindof Present 500 + 5  compounds 1 to 348 + Pasteuria penetrans any onekind of Present  200 + 2000 compounds 1 to 348 + Tebuconazole any onekind of Present 200 + 20  compounds 1 to 348 + Tebuconazole any one kindof Present  500 + 0.5  compounds 1 to 348 + Tebuconazole any one kind ofPresent  200 + 2000 compounds 1 to 348 + Prothioconazole any one kind ofPresent 200 + 20  compounds 1 to 348 + Prothioconazole any one kind ofPresent  500 + 0.5  compounds 1 to 348 + Prothioconazole any one kind ofPresent  200 + 2000 compounds 1 to 348 + Metconazole any one kind ofPresent 200 + 20  compounds 1 to 348 + Metconazole any one kind ofPresent  500 + 0.5  compounds 1 to 348 + Metconazole any one kind ofPresent  200 + 2000 compounds 1 to 348 + Ipconazole any one kind ofPresent 200 + 20  compounds 1 to 348 + Ipconazole any one kind ofPresent  500 + 0.5  compounds 1 to 348 + Ipconazole any one kind ofPresent  200 + 2000 compounds 1 to 348 + Triticonazole any one kind ofPresent 200 + 20  compounds 1 to 348 + Triticonazole any one kind ofPresent  500 + 0.5  compounds 1 to 348 + Triticonazole any one kind ofPresent  200 + 2000 compounds 1 to 348 + Difenoconazole any one kind ofPresent 200 + 20  compounds 1 to 348 + Difenoconazole any one kind ofPresent  500 + 0.5  compounds 1 to 348 + Difenoconazole any one kind ofPresent  200 + 2000 compounds 1 to 348 + Imazalil any one kind ofPresent 200 + 20  compounds 1 to 348 + Imazalil any one kind of Present 500 + 0.5  compounds 1 to 348 + Imazalil any one kind of Present  200 +2000 compounds 1 to 348 + Triadimenol any one kind of Present 200 + 20 compounds 1 to 348 + Triadimenol any one kind of Present  500 + 0.5 compounds 1 to 348 + Triadimenol any one kind of Present  200 + 2000compounds 1 to 348 + Tetraconazole any one kind of Present 200 + 20 compounds 1 to 348 + Tetraconazole any one kind of Present  500 + 0.5 compounds 1 to 348 + Tetraconazole any one kind of Present  200 + 2000compounds 1 to 348 + Flutriafol any one kind of Present 200 + 20 compounds 1 to 348 + Flutriafol any one kind of Present  500 + 0.5 compounds 1 to 348 + Flutriafol any one kind of Present  200 + 2000compounds 1 to 348 + Mandestrobin any one kind of Present 200 + 20 compounds 1 to 348 + Mandestrobin any one kind of Present  500 + 0.5 compounds 1 to 348 + Mandestrobin any one kind of Present  200 + 2000compounds 1 to 348 + Azoxystrobin any one kind of Present 200 + 20 compounds 1 to 348 + Azoxystrobin any one kind of Present  500 + 0.5 compounds 1 to 348 + Azoxystrobin any one kind of Present  200 + 2000compounds 1 to 348 + Pyraclostrobin any one kind of Present 200 + 20 compounds 1 to 348 + Pyraclostrobin any one kind of Present  500 + 0.5 compounds 1 to 348 + Pyraclostrobin any one kind of Present  200 + 2000compounds 1 to 348 + Trifloxystrobin any one kind of Present 200 + 20 compounds 1 to 348 + Trifloxystrobin any one kind of Present  500 + 0.5 compounds 1 to 348 + Trifloxystrobin any one kind of Present  200 + 2000compounds 1 to 348 + Fluoxastrobin any one kind of Present 200 + 20 compounds 1 to 348 + Fluoxastrobin any one kind of Present  500 + 0.5 compounds 1 to 348 + Fluoxastrobin any one kind of Present  200 + 2000compounds 1 to 348 + Picoxystrobin any one kind of Present 200 + 20 compounds 1 to 348 + Picoxystrobin any one kind of Present  500 + 0.5 compounds 1 to 348 + Picoxystrobin any one kind of Present  200 + 2000compounds 1 to 348 + Fenamidone any one kind of Present 200 + 20 compounds 1 to 348 + Fenamidone any one kind of Present  500 + 0.5 compounds 1 to 348 + Fenamidone any one kind of Present  200 + 2000compounds 1 to 348 + Metalaxyl any one kind of Present 200 + 20 compounds 1 to 348 + Metalaxyl any one kind of Present  500 + 0.5 compounds 1 to 348 + Metalaxyl any one kind of Present  200 + 2000compounds 1 to 348 + Metalaxyl M any one kind of Present 200 + 20 compounds 1 to 348 + Metalaxyl M any one kind of Present  500 + 0.5 compounds 1 to 348 + Metalaxyl M any one kind of Present  200 + 2000compounds 1 to 348 + Fludioxonil any one kind of Present 200 + 20 compounds 1 to 348 + Fludioxonil any one kind of Present  500 + 0.5 compounds 1 to 348 + Fludioxonil any one kind of Present  200 + 2000compounds 1 to 348 + Sedaxane any one kind of Present 200 + 20 compounds 1 to 348 + Sedaxane any one kind of Present  500 + 0.5 compounds 1 to 348 + Sedaxane any one kind of Present  200 + 2000compounds 1 to 348 + Penfurufen any one kind of Present 200 + 20 compounds 1 to 348 + Penfurufen any one kind of Present  500 + 0.5 compounds 1 to 348 + Penfurufen any one kind of Present  200 + 2000compounds 1 to 348 + Fluxapyroxad any one kind of Present 200 + 20 compounds 1 to 348 + Fluxapyroxad any one kind of Present  500 + 0.5 compounds 1 to 348 + Fluxapyroxad any one kind of Present  200 + 2000compounds 1 to 348 + Benzovindiflupyr any one kind of Present 200 + 20 compounds 1 to 348 + Benzovindiflupyr any one kind of Present  500 +0.5  compounds 1 to 348 + Benzovindiflupyr any one kind of Present 200 + 2000 compounds 1 to 348 + Boscalid any one kind of Present 200 +20  compounds 1 to 348 + Boscalid any one kind of Present  500 + 0.5 compounds 1 to 348 + Boscalid any one kind of Present  200 + 2000compounds 1 to 348 + Carboxin any one kind of Present 200 + 20 compounds 1 to 348 + Carboxin any one kind of Present  500 + 0.5 compounds 1 to 348 + Carboxin any one kind of Present  200 + 2000compounds 1 to 348 + Penthiopyrad any one kind of Present 200 + 20 compounds 1 to 348 + Penthiopyrad any one kind of Present  500 + 0.5 compounds 1 to 348 + Penthiopyrad any one kind of Present  200 + 2000compounds 1 to 348 + Flutolanil any one kind of Present 200 + 20 compounds 1 to 348 + Flutolanil any one kind of Present  500 + 0.5 compounds 1 to 348 + Flutolanil any one kind of Present  200 + 2000compounds 1 to 348 + Captan any one kind of Present 200 + 20  compounds1 to 348 + Captan any one kind of Present  500 + 0.5  compounds 1 to348 + Captan any one kind of Present  200 + 2000 compounds 1 to 348 +Thiuram any one kind of Present 200 + 20  compounds 1 to 348 + Thiuramany one kind of Present  500 + 0.5  compounds 1 to 348 + Thiuram any onekind of Present  200 + 2000 compounds 1 to 348 + Tolclofos-methyl anyone kind of Present 200 + 20  compounds 1 to 348 + Tolclofos-methyl anyone kind of Present  500 + 0.5  compounds 1 to 348 + Tolclofos-methylany one kind of Present  200 + 2000 compounds 1 to 348 + Thiabendazoleany one kind of Present 200 + 20  compounds 1 to 348 + Thiabendazole anyone kind of Present  500 + 0.5  compounds 1 to 348 + Thiabendazole anyone kind of Present  200 + 2000 compounds 1 to 348 + Ethaboxam any onekind of Present 200 + 20  compounds 1 to 348 + Ethaboxam any one kind ofPresent  500 + 0.5  compounds 1 to 348 + Ethaboxam any one kind ofPresent  200 + 2000 compounds 1 to 348 + Mancozeb any one kind ofPresent 200 + 20  compounds 1 to 348 + Mancozeb any one kind of Present 500 + 0.5  compounds 1 to 348 + Mancozeb any one kind of Present  200 +2000 compounds 1 to 348 + Picarbutrazox any one kind of Present 200 +20  compounds 1 to 348 + Picarbutrazox any one kind of Present  500 +0.5  compounds 1 to 348 + Picarbutrazox any one kind of Present  200 +2000 compounds 1 to 348 + Oxathiapiprolin any one kind of Present 200 +20  compounds 1 to 348 + Oxathiapiprolin any one kind of Present  500 +0.5  compounds 1 to 348 + Oxathiapiprolin any one kind of Present  200 +2000 compounds 1 to 348 + Silthiofam any one kind of Present 200 + 20 compounds 1 to 348 + Silthiofam any one kind of Present  500 + 0.5 compounds 1 to 348 + Silthiofam any one kind of Present  200 + 2000compounds 1 to 348 + Fungicide compound β1 any one kind of Present 200 +20  compounds 1 to 348 + Fungicide compound β1 any one kind of Present 500 + 0.5  compounds 1 to 348 + Fungicide compound β1 any one kind ofPresent  200 + 2000 compounds 1 to 348 + Fungicide compound β2 any onekind of Present 200 + 20  compounds 1 to 348 + Fungicide compound β2 anyone kind of Present  500 + 0.5  compounds 1 to 348 + Fungicide compoundβ2

Next, the Test example is used to show an efficacy of the presentcomposition on controlling harmful arthropods.

Test Example 12

Each 1 mg of the Present compound was dissolved into a 10 μL of themixed solution of xylene:DMF:surfactants (Trade name: Sorpol 3005X,manufactured by TOHO CHEMICAL INDUSTRY CO. LTD)(xylene:DMF:surfactants=4:4:1 (v/v ratio)). Thereto was added watercontaining 0.02% (v/v) of the spreading agent (Trade name: Sindain,manufactured by Sumitomo Chemical Company, Limited) so as to give adiluted solution containing the prescribed concentration of the Presentcompound.

When the commercially available formulation of the present activeingredient was used, each of the commercially available formulation wasdiluted with water containing 0.02 v/v % of the spreader to prepare theprescribed concentration of the diluted solution of the present activeingredient.

Whereas, when the commercially available formulation of the presentactive ingredient was not used, each 1 mg of the present activeingredient was dissolved into a 10 μL of the mixed solution of xylene,DMF and surfactants (xylene, DMF and surfactants=4:4:1 (v/v ratio)).Thereto was added water containing 0.02% by volume of a spreader (Tradename: Sindain, manufactured by Sumitomo Chemical Company, Limited) toprepare a diluted solution containing a prescribed concentration of thepresent active ingredient.

The above prepared diluted solution of the Present compound and theabove prepared diluted solution of the present active ingredient weremixed to prepare the test chemical solution of the compositioncomprising the Present compound and the present active ingredient.

A leaf disk (length 1.5 cm) of the seed leaf of cucumber (Cucumissativus) was placed into each well in a 24 well microplate, and 2wingless adults of a cotton aphid (Aphis gossypii) and 8 nymphs werereleased per 1 well, and the test chemical solution was sprayed in aratio of 20 μL per 1 well, which is referred to as a treated group.

Whereas, 20 μl of water containing 0.02 v/v % of the spreader (Tradename: Sindain, manufactured by Sumitomo Chemical Company, Limited) wassprayed into a well instead of the test drug solution, which wasreferred to as an untreated group.

After the test chemical solution was dried, the upper part of amicroplate was covered with the gas permeable film sheet (Product Name:AeraSeal, manufactured by Excel Scientific Inc.), and 5 days after therelease, the number of the surviving insects of each well was examined.

The controlling value was calculated by the following equation.Controlling value (%)={1−(Tai)/(Cai)}×100wherein the symbols in the formula represent the following descriptions.

Cai: Number of the surviving insects at the time of the investigation inuntreated group;

Tai: Number of the surviving insects at the time of the investigation intreated group;

The result of the test that was done according to Test example 12 isshown below.

Any the present composition wherein the respective concentration of thePresent compound and the present active ingredient is indicated in thefollowing Tables 48 to 61 showed 90% or greater as a controlling valueagainst harmful arthropods.

Table 48

TABLE 48 Concentration Composition (ppm) Present compound 2 +Clothianidin  200 + 2000 Present compound 2 + Clothianidin 500 + 50 Present compound 2 + Imidacloprid  200 + 2000 Present compound 2 +Imidacloprid 500 + 50  Present compound 2 + Thiamethoxam  200 + 2000Present compound 2 + Thiamethoxam 500 + 50  Present compound 2 +Azoxystrobin 200 + 200 Present compound 2 + Azoxystrobin  500 + 0.5 Present compound 2 + Difenoconazole 200 + 200 Present compound 2 +Difenoconazole  500 + 0.5  Present compound 2 + Ethaboxam 200 + 200Present compound 2 + Ethaboxam  500 + 0.5  Present compound 2 +Fludioxonil 200 + 200 Present compound 2 + Fludioxonil  500 + 0.5 Present compound 2 + Fluopyram  200 + 2000 Present compound 2 +Fluopyram  500 + 0.5  Present compound 2 + Fluoxastrobin 200 + 200Present compound 2 + Fluoxastrobin  500 + 0.5  Present compound 2 +Flutolanil 200 + 200 Present compound 2 + Flutolanil  500 + 0.5  Presentcompound 2 + Flutriafol 200 + 200 Present compound 2 + Flutriafol  500 +0.5  Present compound 2 + Fluxapyroxad 200 + 200 Present compound 2 +Fluxapyroxad  500 + 0.5  Present compound 2 + Ipconazole 200 + 200Present compound 2 + Ipconazole  500 + 0.5  Present compound 2 +Mandestrobin 200 + 200 Present compound 2 + Mandestrobin  500 + 0.5 Present compound 2 + Metalaxyl M 200 + 200 Present compound 2 +Metalaxyl M  500 + 0.5  Present compound 2 + Metalaxyl 200 + 200 Presentcompound 2 + Metalaxyl  500 + 0.5  Present compound 2 + Metconazole200 + 200 Present compound 2 + Metconazole  500 + 0.5  Present compound2 + Oxathiapiprolin 200 + 200 Present compound 2 + Oxathiapiprolin 500 + 0.5  Present compound 2 + Penfurufen 200 + 200 Present compound2 + Penfurufen  500 + 0.5  Present compound 2 + Penthiopyrad 200 + 200Present compound 2 + Penthiopyrad  500 + 0.5  Present compound 2 +Picoxystrobin 200 + 200 Present compound 2 + Picoxystrobin  500 + 0.5 Present compound 2 + Prothioconazole 200 + 200 Present compound 2 +Prothioconazole  500 + 0.5  Present compound 2 + Pyraclostrobin 200 +200 Present compound 2 + Pyraclostrobin  500 + 0.5  Present compound 2 +Fungicide compound β2 200 + 200 Present compound 2 + Fungicide compoundβ2  500 + 0.5  Present compound 2 + Sedaxane 200 + 200 Present compound2 + Sedaxane  500 + 0.5  Present compound 2 + Tebuconazole 200 + 200Present compound 2 + Tebuconazole  500 + 0.5  Present compound 2 +Triadimenol 200 + 200 Present compound 2 + Triadimenol  500 + 0.5 Present compound 2 + Trifloxystrobin 200 + 200 Present compound 2 +Trifloxystrobin  500 + 0.5  Present compound 2 + Triticonazole 200 + 200Present compound 2 + Triticonazole  500 + 0.5 

TABLE 49 Concentration Composition (ppm) Present compound 4 +Clothianidin  200 + 2000 Present compound 4 + Clothianidin 500 + 50 Present compound 4 + Imidacloprid  200 + 2000 Present compound 4 +Imidacloprid 500 + 50  Present compound 4 + Thiamethoxam  200 + 2000Present compound 4 + Thiamethoxam 500 + 50  Present compound 4 +Azoxystrobin 200 + 200 Present compound 4 + Azoxystrobin  500 + 0.5 Present compound 4 + Difenoconazole 200 + 200 Present compound 4 +Difenoconazole  500 + 0.5  Present compound 4 + Ethaboxam 200 + 200Present compound 4 + Ethaboxam  500 + 0.5  Present compound 4 +Fludioxonil 200 + 200 Present compound 4 + Fludioxonil  500 + 0.5 Present compound 4 + Fluopyram  200 + 2000 Present compound 4 +Fluopyram  500 + 0.5  Present compound 4 + Fluoxastrobin 200 + 200Present compound 4 + Fluoxastrobin  500 + 0.5  Present compound 4 +Flutolanil 200 + 200 Present compound 4 + Flutolanil  500 + 0.5  Presentcompound 4 + Flutriafol 200 + 200 Present compound 4 + Flutriafol  500 +0.5  Present compound 4 + Fluxapyroxad 200 + 200 Present compound 4 +Fluxapyroxad  500 + 0.5  Present compound 4 + Ipconazole 200 + 200Present compound 4 + Ipconazole  500 + 0.5  Present compound 4 +Mandestrobin 200 + 200 Present compound 4 + Mandestrobin  500 + 0.5 Present compound 4 + Metalaxyl M 200 + 200 Present compound 4 +Metalaxyl M  500 + 0.5  Present compound 4 + Metalaxyl 200 + 200 Presentcompound 4 + Metalaxyl  500 + 0.5  Present compound 4 + Metconazole200 + 200 Present compound 4 + Metconazole  500 + 0.5  Present compound4 + Oxathiapiprolin 200 + 200 Present compound 4 + Oxathiapiprolin 500 + 0.5  Present compound 4 + Penfurufen 200 + 200 Present compound4 + Penfurufen  500 + 0.5  Present compound 4 + Penthiopyrad 200 + 200Present compound 4 + Penthiopyrad  500 + 0.5  Present compound 4 +Picoxystrobin 200 + 200 Present compound 4 + Picoxystrobin  500 + 0.5 Present compound 4 + Prothioconazole 200 + 200 Present compound 4 +Prothioconazole  500 + 0.5  Present compound 4 + Pyraclostrobin 200 +200 Present compound 4 + Pyraclostrobin  500 + 0.5  Present compound 4 +Fungicide compound β2 200 + 200 Present compound 4 + Fungicide compoundβ2  500 + 0.5  Present compound 4 + Sedaxane 200 + 200 Present compound4 + Sedaxane  500 + 0.5  Present compound 4 + Tebuconazole 200 + 200Present compound 4 + Tebuconazole  500 + 0.5  Present compound 4 +Triadimenol 200 + 200 Present compound 4 + Triadimenol  500 + 0.5 Present compound 4 + Trifloxystrobin 200 + 200 Present compound 4 +Trifloxystrobin  500 + 0.5  Present compound 4 + Triticonazole 200 + 200Present compound 4 + Triticonazole  500 + 0.5 

TABLE 50 Concentration Composition (ppm) Present compound 5 +Clothianidin  200 + 2000 Present compound 5 + Clothianidin 500 + 50 Present compound 5 + Imidacloprid  200 + 2000 Present compound 5 +Imidacloprid 500 + 50  Present compound 5 + Thiamethoxam  200 + 2000Present compound 5 + Thiamethoxam 500 + 50  Present compound 5 +Azoxystrobin 200 + 200 Present compound 5 + Azoxystrobin  500 + 0.5 Present compound 5 + Difenoconazole 200 + 200 Present compound 5 +Difenoconazole  500 + 0.5  Present compound 5 + Ethaboxam 200 + 200Present compound 5 + Ethaboxam  500 + 0.5  Present compound 5 +Fludioxonil 200 + 200 Present compound 5 + Fludioxonil  500 + 0.5 Present compound 5 + Fluopyram  200 + 2000 Present compound 5 +Fluopyram  500 + 0.5  Present compound 5 + Fluoxastrobin 200 + 200Present compound 5 + Fluoxastrobin  500 + 0.5  Present compound 5 +Flutolanil 200 + 200 Present compound 5 + Flutolanil  500 + 0.5  Presentcompound 5 + Flutriafol 200 + 200 Present compound 5 + Flutriafol  500 +0.5  Present compound 5 + Fluxapyroxad 200 + 200 Present compound 5 +Fluxapyroxad  500 + 0.5  Present compound 5 + Ipconazole 200 + 200Present compound 5 + Ipconazole  500 + 0.5  Present compound 5 +Mandestrobin 200 + 200 Present compound 5 + Mandestrobin  500 + 0.5 Present compound 5 + Metalaxyl M 200 + 200 Present compound 5 +Metalaxyl M  500 + 0.5  Present compound 5 + Metalaxyl 200 + 200 Presentcompound 5 + Metalaxyl  500 + 0.5  Present compound 5 + Metconazole200 + 200 Present compound 5 + Metconazole  500 + 0.5  Present compound5 + Oxathiapiprolin 200 + 200 Present compound 5 + Oxathiapiprolin 500 + 0.5  Present compound 5 + Penfurufen 200 + 200 Present compound5 + Penfurufen  500 + 0.5  Present compound 5 + Penthiopyrad 200 + 200Present compound 5 + Penthiopyrad  500 + 0.5  Present compound 5 +Picoxystrobin 200 + 200 Present compound 5 + Picoxystrobin  500 + 0.5 Present compound 5 + Prothioconazole 200 + 200 Present compound 5 +Prothioconazole  500 + 0.5  Present compound 5 + Pyraclostrobin 200 +200 Present compound 5 + Pyraclostrobin  500 + 0.5  Present compound 5 +Fungicide compound β2 200 + 200 Present compound 5 + Fungicide compoundβ2  500 + 0.5  Present compound 5 + Sedaxane 200 + 200 Present compound5 + Sedaxane  500 + 0.5  Present compound 5 + Tebuconazole 200 + 200Present compound 5 + Tebuconazole  500 + 0.5  Present compound 5 +Triadimenol 200 + 200 Present compound 5 + Triadimenol  500 + 0.5 Present compound 5 + Trifloxystrobin 200 + 200 Present compound 5 +Trifloxystrobin  500 + 0.5  Present compound 5 + Triticonazole 200 + 200Present compound 5 + Triticonazole  500 + 0.5 

TABLE 51 Concentration Composition (ppm) Present compound 6 +Clothianidin  200 + 2000 Present compound 6 + Clothianidin 500 + 50 Present compound 6 + Imidacloprid  200 + 2000 Present compound 6 +Imidacloprid 500 + 50  Present compound 6 + Thiamethoxam  200 + 2000Present compound 6 + Thiamethoxam 500 + 50  Present compound 6 +Azoxystrobin 200 + 200 Present compound 6 + Azoxystrobin  500 + 0.5 Present compound 6 + Difenoconazole 200 + 200 Present compound 6 +Difenoconazole  500 + 0.5  Present compound 6 + Ethaboxam 200 + 200Present compound 6 + Ethaboxam  500 + 0.5  Present compound 6 +Fludioxonil 200 + 200 Present compound 6 + Fludioxonil  500 + 0.5 Present compound 6 + Fluopyram  200 + 2000 Present compound 6 +Fluopyram  500 + 0.5  Present compound 6 + Fluoxastrobin 200 + 200Present compound 6 + Fluoxastrobin  500 + 0.5  Present compound 6 +Flutolanil 200 + 200 Present compound 6 + Flutolanil  500 + 0.5  Presentcompound 6 + Flutriafol 200 + 200 Present compound 6 + Flutriafol  500 +0.5  Present compound 6 + Fluxapyroxad 200 + 200 Present compound 6 +Fluxapyroxad  500 + 0.5  Present compound 6 + Ipconazole 200 + 200Present compound 6 + Ipconazole  500 + 0.5  Present compound 6 +Mandestrobin 200 + 200 Present compound 6 + Mandestrobin  500 + 0.5 Present compound 6 + Metalaxyl M 200 + 200 Present compound 6 +Metalaxyl M  500 + 0.5  Present compound 6 + Metalaxyl 200 + 200 Presentcompound 6 + Metalaxyl  500 + 0.5  Present compound 6 + Metconazole200 + 200 Present compound 6 + Metconazole  500 + 0.5  Present compound6 + Oxathiapiprolin 200 + 200 Present compound 6 + Oxathiapiprolin 500 + 0.5  Present compound 6 + Penfurufen 200 + 200 Present compound6 + Penfurufen  500 + 0.5  Present compound 6 + Penthiopyrad 200 + 200Present compound 6 + Penthiopyrad  500 + 0.5  Present compound 6 +Picoxystrobin 200 + 200 Present compound 6 + Picoxystrobin  500 + 0.5 Present compound 6 + Prothioconazole 200 + 200 Present compound 6 +Prothioconazole  500 + 0.5  Present compound 6 + Pyraclostrobin 200 +200 Present compound 6 + Pyraclostrobin  500 + 0.5  Present compound 6 +Fungicide compound β2 200 + 200 Present compound 6 + Fungicide compoundβ2  500 + 0.5  Present compound 6 + Sedaxane 200 + 200 Present compound6 + Sedaxane  500 + 0.5  Present compound 6 + Tebuconazole 200 + 200Present compound 6 + Tebuconazole  500 + 0.5  Present compound 6 +Triadimenol 200 + 200 Present compound 6 + Triadimenol  500 + 0.5 Present compound 6 + Trifloxystrobin 200 + 200 Present compound 6 +Trifloxystrobin  500 + 0.5  Present compound 6 + Triticonazole 200 + 200Present compound 6 + Triticonazole  500 + 0.5 

TABLE 52 Concentration Composition (ppm) Present compound 7 +Clothianidin  200 + 2000 Present compound 7 + Clothianidin 500 + 50 Present compound 7 + Imidacloprid  200 + 2000 Present compound 7 +Imidacloprid 500 + 50  Present compound 7 + Thiamethoxam  200 + 2000Present compound 7 + Thiamethoxam 500 + 50  Present compound 7 +Azoxystrobin 200 + 200 Present compound 7 + Azoxystrobin  500 + 0.5 Present compound 7 + Difenoconazole 200 + 200 Present compound 7 +Difenoconazole  500 + 0.5  Present compound 7 + Ethaboxam 200 + 200Present compound 7 + Ethaboxam  500 + 0.5  Present compound 7 +Fludioxonil 200 + 200 Present compound 7 + Fludioxonil  500 + 0.5 Present compound 7 + Fluopyram  200 + 2000 Present compound 7 +Fluopyram  500 + 0.5  Present compound 7 + Fluoxastrobin 200 + 200Present compound 7 + Fluoxastrobin  500 + 0.5  Present compound 7 +Flutolanil 200 + 200 Present compound 7 + Flutolanil  500 + 0.5  Presentcompound 7 + Flutriafol 200 + 200 Present compound 7 + Flutriafol  500 +0.5  Present compound 7 + Fluxapyroxad 200 + 200 Present compound 7 +Fluxapyroxad  500 + 0.5  Present compound 7 + Ipconazole 200 + 200Present compound 7 + Ipconazole  500 + 0.5  Present compound 7 +Mandestrobin 200 + 200 Present compound 7 + Mandestrobin  500 + 0.5 Present compound 7 + Metalaxyl M 200 + 200 Present compound 7 +Metalaxyl M  500 + 0.5  Present compound 7 + Metalaxyl 200 + 200 Presentcompound 7 + Metalaxyl  500 + 0.5  Present compound 7 + Metconazole200 + 200 Present compound 7 + Metconazole  500 + 0.5  Present compound7 + Oxathiapiprolin 200 + 200 Present compound 7 + Oxathiapiprolin 500 + 0.5  Present compound 7 + Penfurufen 200 + 200 Present compound7 + Penfurufen  500 + 0.5  Present compound 7 + Penthiopyrad 200 + 200Present compound 7 + Penthiopyrad  500 + 0.5  Present compound 7 +Picoxystrobin 200 + 200 Present compound 7 + Picoxystrobin  500 + 0.5 Present compound 7 + Prothioconazole 200 + 200 Present compound 7 +Prothioconazole  500 + 0.5  Present compound 7 + Pyraclostrobin 200 +200 Present compound 7 + Pyraclostrobin  500 + 0.5  Present compound 7 +Fungicide compound β2 200 + 200 Present compound 7 + Fungicide compoundβ2  500 + 0.5  Present compound 7 + Sedaxane 200 + 200 Present compound7 + Sedaxane  500 + 0.5  Present compound 7 + Tebuconazole 200 + 200Present compound 7 + Tebuconazole  500 + 0.5  Present compound 7 +Triadimenol 200 + 200 Present compound 7 + Triadimenol  500 + 0.5 Present compound 7 + Trifloxystrobin 200 + 200 Present compound 7 +Trifloxystrobin  500 + 0.5  Present compound 7 + Triticonazole 200 + 200Present compound 7 + Triticonazole  500 + 0.5 

TABLE 53 Concentration Composition (ppm) Present compound 8 +Clothianidin  200 + 2000 Present compound 8 + Clothianidin 500 + 50 Present compound 8 + Imidacloprid  200 + 2000 Present compound 8 +Imidacloprid 500 + 50  Present compound 8 + Thiamethoxam  200 + 2000Present compound 8 + Thiamethoxam 500 + 50  Present compound 8 +Azoxystrobin 200 + 200 Present compound 8 + Azoxystrobin  500 + 0.5 Present compound 8 + Difenoconazole 200 + 200 Present compound 8 +Difenoconazole  500 + 0.5  Present compound 8 + Ethaboxam 200 + 200Present compound 8 + Ethaboxam  500 + 0.5  Present compound 8 +Fludioxonil 200 + 200 Present compound 8 + Fludioxonil  500 + 0.5 Present compound 8 + Fluopyram  200 + 2000 Present compound 8 +Fluopyram  500 + 0.5  Present compound 8 + Fluoxastrobin 200 + 200Present compound 8 + Fluoxastrobin  500 + 0.5  Present compound 8 +Flutolanil 200 + 200 Present compound 8 + Flutolanil  500 + 0.5  Presentcompound 8 + Flutriafol 200 + 200 Present compound 8 + Flutriafol  500 +0.5  Present compound 8 + Fluxapyroxad 200 + 200 Present compound 8 +Fluxapyroxad  500 + 0.5  Present compound 8 + Ipconazole 200 + 200Present compound 8 + Ipconazole  500 + 0.5  Present compound 8 +Mandestrobin 200 + 200 Present compound 8 + Mandestrobin  500 + 0.5 Present compound 8 + Metalaxyl M 200 + 200 Present compound 8 +Metalaxyl M  500 + 0.5  Present compound 8 + Metalaxyl 200 + 200 Presentcompound 8 + Metalaxyl  500 + 0.5  Present compound 8 + Metconazole200 + 200 Present compound 8 + Metconazole  500 + 0.5  Present compound8 + Oxathiapiprolin 200 + 200 Present compound 8 + Oxathiapiprolin 500 + 0.5  Present compound 8 + Penfurufen 200 + 200 Present compound8 + Penfurufen  500 + 0.5  Present compound 8 + Penthiopyrad 200 + 200Present compound 8 + Penthiopyrad  500 + 0.5  Present compound 8 +Picoxystrobin 200 + 200 Present compound 8 + Picoxystrobin  500 + 0.5 Present compound 8 + Prothioconazole 200 + 200 Present compound 8 +Prothioconazole  500 + 0.5  Present compound 8 + Pyraclostrobin 200 +200 Present compound 8 + Pyraclostrobin  500 + 0.5  Present compound 8 +Fungicide compound β2 200 + 200 Present compound 8 + Fungicide compoundβ2  500 + 0.5  Present compound 8 + Sedaxane 200 + 200 Present compound8 + Sedaxane  500 + 0.5  Present compound 8 + Tebuconazole 200 + 200Present compound 8 + Tebuconazole  500 + 0.5  Present compound 8 +Triadimenol 200 + 200 Present compound 8 + Triadimenol  500 + 0.5 Present compound 8 + Trifloxystrobin 200 + 200 Present compound 8 +Trifloxystrobin  500 + 0.5  Present compound 8 + Triticonazole 200 + 200Present compound 8 + Triticonazole  500 + 0.5 

TABLE 54 Concentration Composition (ppm) Present compound 9 +Clothianidin  200 + 2000 Present compound 9 + Clothianidin 500 + 50 Present compound 9 + Imidacloprid  200 + 2000 Present compound 9 +Imidacloprid 500 + 50  Present compound 9 + Thiamethoxam  200 + 2000Present compound 9 + Thiamethoxam 500 + 50  Present compound 9 +Azoxystrobin 200 + 200 Present compound 9 + Azoxystrobin  500 + 0.5 Present compound 9 + Difenoconazole 200 + 200 Present compound 9 +Difenoconazole  500 + 0.5  Present compound 9 + Ethaboxam 200 + 200Present compound 9 + Ethaboxam  500 + 0.5  Present compound 9 +Fludioxonil 200 + 200 Present compound 9 + Fludioxonil  500 + 0.5 Present compound 9 + Fluopyram  200 + 2000 Present compound 9 +Fluopyram  500 + 0.5  Present compound 9 + Fluoxastrobin 200 + 200Present compound 9 + Fluoxastrobin  500 + 0.5  Present compound 9 +Flutolanil 200 + 200 Present compound 9 + Flutolanil  500 + 0.5  Presentcompound 9 + Flutriafol 200 + 200 Present compound 9 + Flutriafol  500 +0.5  Present compound 9 + Fluxapyroxad 200 + 200 Present compound 9 +Fluxapyroxad  500 + 0.5  Present compound 9 + Ipconazole 200 + 200Present compound 9 + Ipconazole  500 + 0.5  Present compound 9 +Mandestrobin 200 + 200 Present compound 9 + Mandestrobin  500 + 0.5 Present compound 9 + Metalaxyl M 200 + 200 Present compound 9 +Metalaxyl M  500 + 0.5  Present compound 9 + Metalaxyl 200 + 200 Presentcompound 9 + Metalaxyl  500 + 0.5  Present compound 9 + Metconazole200 + 200 Present compound 9 + Metconazole  500 + 0.5  Present compound9 + Oxathiapiprolin 200 + 200 Present compound 9 + Oxathiapiprolin 500 + 0.5  Present compound 9 + Penfurufen 200 + 200 Present compound9 + Penfurufen  500 + 0.5  Present compound 9 + Penthiopyrad 200 + 200Present compound 9 + Penthiopyrad  500 + 0.5  Present compound 9 +Picoxystrobin 200 + 200 Present compound 9 + Picoxystrobin  500 + 0.5 Present compound 9 + Prothioconazole 200 + 200 Present compound 9 +Prothioconazole  500 + 0.5  Present compound 9 + Pyraclostrobin 200 +200 Present compound 9 + Pyraclostrobin  500 + 0.5  Present compound 9 +Fungicide compound β2 200 + 200 Present compound 9 + Fungicide compoundβ2  500 + 0.5  Present compound 9 + Sedaxane 200 + 200 Present compound9 + Sedaxane  500 + 0.5  Present compound 9 + Tebuconazole 200 + 200Present compound 9 + Tebuconazole  500 + 0.5  Present compound 9 +Triadimenol 200 + 200 Present compound 9 + Triadimenol  500 + 0.5 Present compound 9 + Trifloxystrobin 200 + 200 Present compound 9 +Trifloxystrobin  500 + 0.5  Present compound 9 + Triticonazole 200 + 200Present compound 9 + Triticonazole  500 + 0.5 

TABLE 55 Concentration Composition (ppm) Present compound 10 +Clothianidin 200 + 2000 Present compound 10 + Clothianidin 500 + 50Present compound 10 + Imidacloprid 200 + 2000 Present compound 10 +Imidacloprid 500 + 50 Present compound 10 + Thiamethoxam 200 + 2000Present compound 10 + Thiamethoxam 500 + 50 Present compound 10 +Azoxystrobin 200 + 200 Present compound 10 + Azoxystrobin 500 + 0.5Present compound 10 + Difenoconazole 200 + 200 Present compound 10 +Difenoconazole 500 + 0.5 Present compound 10 + Ethaboxam 200 + 200Present compound 10 + Ethaboxam 500 + 0.5 Present compound 10 +Fludioxonil 200 + 200 Present compound 10 + Fludioxonil 500 + 0.5Present compound 10 + Fluopyram 200 + 2000 Present compound 10 +Fluopyram 500 + 0.5 Present compound 10 + Fluoxastrobin 200 + 200Present compound 10 + Fluoxastrobin 500 + 0.5 Present compound 10 +Flutolanil 200 + 200 Present compound 10 + Flutolanil 500 + 0.5 Presentcompound 10 + Flutriafol 200 + 200 Present compound 10 + Flutriafol500 + 0.5 Present compound 10 + Fluxapyroxad 200 + 200 Present compound10 + Fluxapyroxad 500 + 0.5 Present compound 10 + Ipconazole 200 + 200Present compound 10 + Ipconazole 500 + 0.5 Present compound 10 +Mandestrobin 200 + 200 Present compound 10 + Mandestrobin 500 + 0.5Present compound 10 + Metalaxyl M 200 + 200 Present compound 10 +Metalaxyl M 500 + 0.5 Present compound 10 + Metalaxyl 200 + 200 Presentcompound 10 + Metalaxyl 500 + 0.5 Present compound 10 + Metconazole200 + 200 Present compound 10 + Metconazole 500 + 0.5 Present compound10 + Oxathiapiprolin 200 + 200 Present compound 10 + Oxathiapiprolin500 + 0.5 Present compound 10 + Penfurufen 200 + 200 Present compound10 + Penfurufen 500 + 0.5 Present compound 10 + Penthiopyrad 200 + 200Present compound 10 + Penthiopyrad 500 + 0.5 Present compound 10 +Picoxystrobin 200 + 200 Present compound 10 + Picoxystrobin 500 + 0.5Present compound 10 + Prothioconazole 200 + 200 Present compound 10 +Prothioconazole 500 + 0.5 Present compound 10 + Pyraclostrobin 200 + 200Present compound 10 + Pyraclostrobin 500 + 0.5 Present compound 10 +Fungicide 200 + 200 Present compound 10 + Fungicide 500 + 0.5 Presentcompound 10 + Sedaxane 200 + 200 Present compound 10 + Sedaxane 500 +0.5 Present compound 10 + Tebuconazole 200 + 200 Present compound 10 +Tebuconazole 500 + 0.5 Present compound 10 + Triadimenol 200 + 200Present compound 10 + Triadimenol 500 + 0.5 Present compound 10 +Trifloxystrobin 200 + 200 Present compound 10 + Trifloxystrobin 500 +0.5 Present compound 10 + Triticonazole 200 + 200 Present compound 10 +Triticonazole 500 + 0.5

TABLE 56 Concentration Composition (ppm) Present compound 11 +Clothianidin 200 + 2000 Present compound 11 + Clothianidin 500 + 50Present compound 11 + Imidacloprid 200 + 2000 Present compound 11 +Imidacloprid 500 + 50 Present compound 11 + Thiamethoxam 200 + 2000Present compound 11 + Thiamethoxam 500 + 50 Present compound 11 +Azoxystrobin 200 + 200 Present compound 11 + Azoxystrobin 500 + 0.5Present compound 11 + Difenoconazole 200 + 200 Present compound 11 +Difenoconazole 500 + 0.5 Present compound 11 + Ethaboxam 200 + 200Present compound 11 + Ethaboxam 500 + 0.5 Present compound 11 +Fludioxonil 200 + 200 Present compound 11 + Fludioxonil 500 + 0.5Present compound 11 + Fluopyram 200 + 2000 Present compound 11 +Fluopyram 500 + 0.5 Present compound 11 + Fluoxastrobin 200 + 200Present compound 11 + Fluoxastrobin 500 + 0.5 Present compound 11 +Flutolanil 200 + 200 Present compound 11 + Flutolanil 500 + 0.5 Presentcompound 11 + Flutriafol 200 + 200 Present compound 11 + Flutriafol500 + 0.5 Present compound 11 + Fluxapyroxad 200 + 200 Present compound11 + Fluxapyroxad 500 + 0.5 Present compound 11 + Ipconazole 200 + 200Present compound 11 + Ipconazole 500 + 0.5 Present compound 11 +Mandestrobin 200 + 200 Present compound 11 + Mandestrobin 500 + 0.5Present compound 11 + Metalaxyl M 200 + 200 Present compound 11 +Metalaxyl M 500 + 0.5 Present compound 11 + Metalaxyl 200 + 200 Presentcompound 11 + Metalaxyl 500 + 0.5 Present compound 11 + Metconazole200 + 200 Present compound 11 + Metconazole 500 + 0.5 Present compound11 + Oxathiapiprolin 200 + 200 Present compound 11 + Oxathiapiprolin500 + 0.5 Present compound 11 + Penfurufen 200 + 200 Present compound11 + Penfurufen 500 + 0.5 Present compound 11 + Penthiopyrad 200 + 200Present compound 11 + Penthiopyrad 500 + 0.5 Present compound 11 +Picoxystrobin 200 + 200 Present compound 11 + Picoxystrobin 500 + 0.5Present compound 11 + Prothioconazole 200 + 200 Present compound 11 +Prothioconazole 500 + 0.5 Present compound 11 + Pyraclostrobin 200 + 200Present compound 11 + Pyraclostrobin 500 + 0.5 Present compound 11 +Fungicide 200 + 200 Present compound 11 + Fungicide 500 + 0.5 Presentcompound 11 + Sedaxane 200 + 200 Present compound 11 + Sedaxane 500 +0.5 Present compound 11 + Tebuconazole 200 + 200 Present compound 11 +Tebuconazole 500 + 0.5 Present compound 11 + Triadimenol 200 + 200Present compound 11 + Triadimenol 500 + 0.5 Present compound 11 +Trifloxystrobin 200 + 200 Present compound 11 + Trifloxystrobin 500 +0.5 Present compound 11 + Triticonazole 200 + 200 Present compound 11 +Triticonazole 500 + 0.5

TABLE 57 Concentration Composition (ppm) Present compound 12 +Clothianidin 200 + 2000 Present compound 12 + Clothianidin 500 + 50Present compound 12 + Imidacloprid 200 + 2000 Present compound 12 +Imidacloprid 500 + 50 Present compound 12 + Thiamethoxam 200 + 2000Present compound 12 + Thiamethoxam 500 + 50 Present compound 12 +Azoxystrobin 200 + 200 Present compound 12 + Azoxystrobin 500 + 0.5Present compound 12 + Difenoconazole 200 + 200 Present compound 12 +Difenoconazole 500 + 0.5 Present compound 12 + Ethaboxam 200 + 200Present compound 12 + Ethaboxam 500 + 0.5 Present compound 12 +Fludioxonil 200 + 200 Present compound 12 + Fludioxonil 500 + 0.5Present compound 12 + Fluopyram 200 + 2000 Present compound 12 +Fluopyram 500 + 0.5 Present compound 12 + Fluoxastrobin 200 + 200Present compound 12 + Fluoxastrobin 500 + 0.5 Present compound 12 +Flutolanil 200 + 200 Present compound 12 + Flutolanil 500 + 0.5 Presentcompound 12 + Flutriafol 200 + 200 Present compound 12 + Flutriafol500 + 0.5 Present compound 12 + Fluxapyroxad 200 + 200 Present compound12 + Fluxapyroxad 500 + 0.5 Present compound 12 + Ipconazole 200 + 200Present compound 12 + Ipconazole 500 + 0.5 Present compound 12 +Mandestrobin 200 + 200 Present compound 12 + Mandestrobin 500 + 0.5Present compound 12 + Metalaxyl M 200 + 200 Present compound 12 +Metalaxyl M 500 + 0.5 Present compound 12 + Metalaxyl 200 + 200 Presentcompound 12 + Metalaxyl 500 + 0.5 Present compound 12 + Metconazole200 + 200 Present compound 12 + Metconazole 500 + 0.5 Present compound12 + Oxathiapiprolin 200 + 200 Present compound 12 + Oxathiapiprolin500 + 0.5 Present compound 12 + Penfurufen 200 + 200 Present compound12 + Penfurufen 500 + 0.5 Present compound 12 + Penthiopyrad 200 + 200Present compound 12 + Penthiopyrad 500 + 0.5 Present compound 12 +Picoxystrobin 200 + 200 Present compound 12 + Picoxystrobin 500 + 0.5Present compound 12 + Prothioconazole 200 + 200 Present compound 12 +Prothioconazole 500 + 0.5 Present compound 12 + Pyraclostrobin 200 + 200Present compound 12 + Pyraclostrobin 500 + 0.5 Present compound 12 +Fungicide compound β2 200 + 200 Present compound 12 + Fungicide compoundβ2 500 + 0.5 Present compound 12 + Sedaxane 200 + 200 Present compound12 + Sedaxane 500 + 0.5 Present compound 12 + Tebuconazole 200 + 200Present compound 12 + Tebuconazole 500 + 0.5 Present compound 12 +Triadimenol 200 + 200 Present compound 12 + Triadimenol 500 + 0.5Present compound 12 + Trifloxystrobin 200 + 200 Present compound 12 +Trifloxystrobin 500 + 0.5 Present compound 12 + Triticonazole 200 + 200Present compound 12 + Triticonazole 500 + 0.5

TABLE 58 Concentration Composition (ppm) Present compound 13 +Clothianidin 200 + 2000 Present compound 13 + Clothianidin 500 + 50Present compound 13 + Imidacloprid 200 + 2000 Present compound 13 +Imidacloprid 500 + 50 Present compound 13 + Thiamethoxam 200 + 2000Present compound 13 + Thiamethoxam 500 + 50 Present compound 13 +Azoxystrobin 200 + 200 Present compound 13 + Azoxystrobin 500 + 0.5Present compound 13 + Difenoconazole 200 + 200 Present compound 13 +Difenoconazole 500 + 0.5 Present compound 13 + Ethaboxam 200 + 200Present compound 13 + Ethaboxam 500 + 0.5 Present compound 13 +Fludioxonil 200 + 200 Present compound 13 + Fludioxonil 500 + 0.5Present compound 13 + Fluopyram 200 + 2000 Present compound 13 +Fluopyram 500 + 0.5 Present compound 13 + Fluoxastrobin 200 + 200Present compound 13 + Fluoxastrobin 500 + 0.5 Present compound 13 +Flutolanil 200 + 200 Present compound 13 + Flutolanil 500 + 0.5 Presentcompound 13 + Flutriafol 200 + 200 Present compound 13 + Flutriafol500 + 0.5 Present compound 13 + Fluxapyroxad 200 + 200 Present compound13 + Fluxapyroxad 500 + 0.5 Present compound 13 + Ipconazole 200 + 200Present compound 13 + Ipconazole 500 + 0.5 Present compound 13 +Mandestrobin 200 + 200 Present compound 13 + Mandestrobin 500 + 0.5Present compound 13 + Metalaxyl M 200 + 200 Present compound 13 +Metalaxyl M 500 + 0.5 Present compound 13 + Metalaxyl 200 + 200 Presentcompound 13 + Metalaxyl 500 + 0.5 Present compound 13 + Metconazole200 + 200 Present compound 13 + Metconazole 500 + 0.5 Present compound13 + Oxathiapiprolin 200 + 200 Present compound 13 + Oxathiapiprolin500 + 0.5 Present compound 13 + Penfurufen 200 + 200 Present compound13 + Penfurufen 500 + 0.5 Present compound 13 + Penthiopyrad 200 + 200Present compound 13 + Penthiopyrad 500 + 0.5 Present compound 13 +Picoxystrobin 200 + 200 Present compound 13 + Picoxystrobin 500 + 0.5Present compound 13 + Prothioconazole 200 + 200 Present compound 13 +Prothioconazole 500 + 0.5 Present compound 13 + Pyraclostrobin 200 + 200Present compound 13 + Pyraclostrobin 500 + 0.5 Present compound 13 +Fungicide compound β2 200 + 200 Present compound 13 + Fungicide compoundβ2 500 + 0.5 Present compound 13 + Sedaxane 200 + 200 Present compound13 + Sedaxane 500 + 0.5 Present compound 13 + Tebuconazole 200 + 200Present compound 13 + Tebuconazole 500 + 0.5 Present compound 13 +Triadimenol 200 + 200 Present compound 13 + Triadimenol 500 + 0.5Present compound 13 + Trifloxystrobin 200 + 200 Present compound 13 +Trifloxystrobin 500 + 0.5 Present compound 13 + Triticonazole 200 + 200Present compound 13 + Triticonazole 500 + 0.5

TABLE 59 Concentration Composition (ppm) Present compound 16 +Clothianidin 200 + 2000 Present compound 16 + Clothianidin 500 + 50Present compound 16 + Imidacloprid 200 + 2000 Present compound 16 +Imidacloprid 500 + 50 Present compound 16 + Thiamethoxam 200 + 2000Present compound 16 + Thiamethoxam 500 + 50 Present compound 16 +Azoxystrobin 200 + 200 Present compound 16 + Azoxystrobin 500 + 0.5Present compound 16 + Difenoconazole 200 + 200 Present compound 16 +Difenoconazole 500 + 0.5 Present compound 16 + Ethaboxam 200 + 200Present compound 16 + Ethaboxam 500 + 0.5 Present compound 16 +Fludioxonil 200 + 200 Present compound 16 + Fludioxonil 500 + 0.5Present compound 16 + Fluopyram 200 + 2000 Present compound 16 +Fluopyram 500 + 0.5 Present compound 16 + Fluoxastrobin 200 + 200Present compound 16 + Fluoxastrobin 500 + 0.5 Present compound 16 +Flutolanil 200 + 200 Present compound 16 + Flutolanil 500 + 0.5 Presentcompound 16 + Flutriafol 200 + 200 Present compound 16 + Flutriafol500 + 0.5 Present compound 16 + Fluxapyroxad 200 + 200 Present compound16 + Fluxapyroxad 500 + 0.5 Present compound 16 + Ipconazole 200 + 200Present compound 16 + Ipconazole 500 + 0.5 Present compound 16 +Mandestrobin 200 + 200 Present compound 16 + Mandestrobin 500 + 0.5Present compound 16 + Metalaxyl M 200 + 200 Present compound 16 +Metalaxyl M 500 + 0.5 Present compound 16 + Metalaxyl 200 + 200 Presentcompound 16 + Metalaxyl 500 + 0.5 Present compound 16 + Metconazole200 + 200 Present compound 16 + Metconazole 500 + 0.5 Present compound16 + Oxathiapiprolin 200 + 200 Present compound 16 + Oxathiapiprolin500 + 0.5 Present compound 16 + Penfurufen 200 + 200 Present compound16 + Penfurufen 500 + 0.5 Present compound 16 + Penthiopyrad 200 + 200Present compound 16 + Penthiopyrad 500 + 0.5 Present compound 16 +Picoxystrobin 200 + 200 Present compound 16 + Picoxystrobin 500 + 0.5Present compound 16 + Prothioconazole 200 + 200 Present compound 16 +Prothioconazole 500 + 0.5 Present compound 16 + Pyraclostrobin 200 + 200Present compound 16 + Pyraclostrobin 500 + 0.5 Present compound 16 +Fungicide compound β2 200 + 200 Present compound 16 + Fungicide compoundβ2 500 + 0.5 Present compound 16 + Sedaxane 200 + 200 Present compound16 + Sedaxane 500 + 0.5 Present compound 16 + Tebuconazole 200 + 200Present compound 16 + Tebuconazole 500 + 0.5 Present compound 16 +Triadimenol 200 + 200 Present compound 16 + Triadimenol 500 + 0.5Present compound 16 + Trifloxystrobin 200 + 200 Present compound 16 +Trifloxystrobin 500 + 0.5 Present compound 16 + Triticonazole 200 + 200Present compound 16 + Triticonazole 500 + 0.5

TABLE 60 Concentration Composition (ppm) Present compound 18 +Clothianidin 200 + 2000 Present compound 18 + Clothianidin 500 + 50Present compound 18 + Imidacloprid 200 + 2000 Present compound 18 +Imidacloprid 500 + 50 Present compound 18 + Thiamethoxam 200 + 2000Present compound 18 + Thiamethoxam 500 + 50 Present compound 18 +Azoxystrobin 200 + 200 Present compound 18 + Azoxystrobin 500 + 0.5Present compound 18 + Difenoconazole 200 + 200 Present compound 18 +Difenoconazole 500 + 0.5 Present compound 18 + Ethaboxam 200 + 200Present compound 18 + Ethaboxam 500 + 0.5 Present compound 18 +Fludioxonil 200 + 200 Present compound 18 + Fludioxonil 500 + 0.5Present compound 18 + Fluopyram 200 + 2000 Present compound 18 +Fluopyram 500 + 0.5 Present compound 18 + Fluoxastrobin 200 + 200Present compound 18 + Fluoxastrobin 500 + 0.5 Present compound 18 +Flutolanil 200 + 200 Present compound 18 + Flutolanil 500 + 0.5 Presentcompound 18 + Flutriafol 200 + 200 Present compound 18 + Flutriafol500 + 0.5 Present compound 18 + Fluxapyroxad 200 + 200 Present compound18 + Fluxapyroxad 500 + 0.5 Present compound 18 + Ipconazole 200 + 200Present compound 18 + Ipconazole 500 + 0.5 Present compound 18 +Mandestrobin 200 + 200 Present compound 18 + Mandestrobin 500 + 0.5Present compound 18 + Metalaxyl M 200 + 200 Present compound 18 +Metalaxyl M 500 + 0.5 Present compound 18 + Metalaxyl 200 + 200 Presentcompound 18 + Metalaxyl 500 + 0.5 Present compound 18 + Metconazole200 + 200 Present compound 18 + Metconazole 500 + 0.5 Present compound18 + Oxathiapiprolin 200 + 200 Present compound 18 + Oxathiapiprolin500 + 0.5 Present compound 18 + Penfurufen 200 + 200 Present compound18 + Penfurufen 500 + 0.5 Present compound 18 + Penthiopyrad 200 + 200Present compound 18 + Penthiopyrad 500 + 0.5 Present compound 18 +Picoxystrobin 200 + 200 Present compound 18 + Picoxystrobin 500 + 0.5Present compound 18 + Prothioconazole 200 + 200 Present compound 18 +Prothioconazole 500 + 0.5 Present compound 18 + Pyraclostrobin 200 + 200Present compound 18 + Pyraclostrobin 500 + 0.5 Present compound 18 +Fungicide compound β2 200 + 200 Present compound 18 + Fungicide compoundβ2 500 + 0.5 Present compound 18 + Sedaxane 200 + 200 Present compound18 + Sedaxane 500 + 0.5 Present compound 18 + Tebuconazole 200 + 200Present compound 18 + Tebuconazole 500 + 0.5 Present compound 18 +Triadimenol 200 + 200 Present compound 18 + Triadimenol 500 + 0.5Present compound 18 + Trifloxystrobin 200 + 200 Present compound 18 +Trifloxystrobin 500 + 0.5 Present compound 18 + Triticonazole 200 + 200Present compound 18 + Triticonazole 500 + 0.5

TABLE 61 Concentration Composition (ppm) Present compound 24 +Clothianidin 200 + 2000 Present compound 24 + Clothianidin 500 + 50Present compound 24 + Imidacloprid 200 + 2000 Present compound 24 +Imidacloprid 500 + 50 Present compound 24 + Thiamethoxam 200 + 2000Present compound 24 + Thiamethoxam 500 + 50 Present compound 24 +Azoxystrobin 200 + 200 Present compound 24 + Azoxystrobin 500 + 0.5Present compound 24 + Difenoconazole 200 + 200 Present compound 24 +Difenoconazole 500 + 0.5 Present compound 24 + Ethaboxam 200 + 200Present compound 24 + Ethaboxam 500 + 0.5 Present compound 24 +Fludioxonil 200 + 200 Present compound 24 + Fludioxonil 500 + 0.5Present compound 24 + Fluopyram 200 + 2000 Present compound 24 +Fluopyram 500 + 0.5 Present compound 24 + Fluoxastrobin 200 + 200Present compound 24 + Fluoxastrobin 500 + 0.5 Present compound 24 +Flutolanil 200 + 200 Present compound 24 + Flutolanil 500 + 0.5 Presentcompound 24 + Flutriafol 200 + 200 Present compound 24 + Flutriafol500 + 0.5 Present compound 24 + Fluxapyroxad 200 + 200 Present compound24 + Fluxapyroxad 500 + 0.5 Present compound 24 + Ipconazole 200 + 200Present compound 24 + Ipconazole 500 + 0.5 Present compound 24 +Mandestrobin 200 + 200 Present compound 24 + Mandestrobin 500 + 0.5Present compound 24 + Metalaxyl M 200 + 200 Present compound 24 +Metalaxyl M 500 + 0.5 Present compound 24 + Metalaxyl 200 + 200 Presentcompound 24 + Metalaxyl 500 + 0.5 Present compound 24 + Metconazole200 + 200 Present compound 24 + Metconazole 500 + 0.5 Present compound24 + Oxathiapiprolin 200 + 200 Present compound 24 + Oxathiapiprolin500 + 0.5 Present compound 24 + Penfurufen 200 + 200 Present compound24 + Penfurufen 500 + 0.5 Present compound 24 + Penthiopyrad 200 + 200Present compound 24 + Penthiopyrad 500 + 0.5 Present compound 24 +Picoxystrobin 200 + 200 Present compound 24 + Picoxystrobin 500 + 0.5Present compound 24 + Prothioconazole 200 + 200 Present compound 24 +Prothioconazole 500 + 0.5 Present compound 24 + Pyraclostrobin 200 + 200Present compound 24 + Pyraclostrobin 500 + 0.5 Present compound 24 +Fungicide compound β2 200 + 200 Present compound 24 + Fungicide compoundβ2 500 + 0.5 Present compound 24 + Sedaxane 200 + 200 Present compound24 + Sedaxane 500 + 0.5 Present compound 24 + Tebuconazole 200 + 200Present compound 24 + Tebuconazole 500 + 0.5 Present compound 24 +Triadimenol 200 + 200 Present compound 24 + Triadimenol 500 + 0.5Present compound 24 + Trifloxystrobin 200 + 200 Present compound 24 +Trifloxystrobin 500 + 0.5 Present compound 24 + Triticonazole 200 + 200Present compound 24 + Triticonazole 500 + 0.5

INDUSTRIAL APPLICABILITY

The Present compound shows an excellent control effect against a harmfularthropod. Also, the composition comprising the Present compound and oneor more kinds of ingredients selected from the group consisting of Group(a), Group (b), Group (c) and Group (d) shows an excellent controleffect against a harmful arthropod.

The invention claimed is:
 1. A compound represented by formula (M-4):

wherein V represents a halogen atom; A¹ represents a nitrogen atom or aCR⁴; R⁴ represents a hydrogen atom, a OR²⁷, a NR²⁷R²⁸, a cyano group, anitro group, or a halogen atom; R²⁷ and R²⁸ represent independently ofeach other, a hydrogen atom, or a C1-C6 alkyl group optionally havingone or more halogen atoms; R² represents a C1-C6 alkyl group optionallyhaving one or more halogen atoms, a cyclopropylmethyl group, or acyclopropyl group; q represents 0, 1, 2, or 3; R³ representsindependently of each other a C1-C6 chain hydrocarbon group optionallyhaving one or more substituents selected from Group B, a phenyl groupoptionally having one or more substituents selected from Group D, a 5 or6 membered aromatic heterocyclic group optionally having one or moresubstituents selected from Group D, a OR¹², a NR¹¹R¹², aNR^(11a)R^(12a), a NR²⁹NR¹¹R¹², a NR²⁹OR¹¹, A NR¹¹C(O)R¹³, aNR²⁹NR¹¹C(O)R¹³, a NR¹¹C(O)OR¹⁴, a NR²⁹NR¹¹C(O)OR¹⁴, a NR¹¹C(O)NR¹⁵R¹⁶,a NR²⁴NR¹¹C(O)NR¹⁵R¹⁶, a N═CHNR¹⁵R¹⁶, a N═S(O)_(x)R¹⁵R¹⁶, a S(O)_(y)R¹⁵,a C(O)OR¹⁷, a C(O)NR¹¹R¹², a cyano group, a nitro group, or a halogenatom, and when q is 2 or 3, a plurality of R³ may be identical ordifferent; x represents 0 or 1; y represents 0, 1, or 2; R¹¹, R¹⁷, R¹⁸,R¹⁹, R²⁴ and R²⁹ represent independently of each other a hydrogen atom,or a C1-C6 chain hydrocarbon group optionally having one or more halogenatoms; R¹² represents a hydrogen atom, a C1-C6 chain hydrocarbon groupoptionally having one or more halogen atoms, a C1-C6 alkyl group havingone substituent selected from Group F, or a S(O)₂R²³; R²³ represents aC1-C6 chain hydrocarbon group optionally having one or more halogenatoms, or a phenyl group optionally having one or more substituentsselected from Group D; R^(11a) and R^(12a) combine together with anitrogen atom to which they are attached to form a 3 to 7 memberednonaromatic heterocyclic group optionally having one or moresubstituents selected from Group E {the 3 to 7 membered nonaromaticheterocyclic group represents aziridine, azetidine, pyrrolidine,imidazoline, imidazolidine, piperidine, tetrahydropyrimidine,hexahydropyrimidine, piperazine, azepane, oxazolidine, isooxazolidine,1,3-oxazinane, morpholine, 1,4-oxazepane, thiazolidine, isothiazolidine,1,3-thiazinane, thiomorpholine, or 1,4-thiazepane}; R¹³ represents ahydrogen atom, a C1-C6 chain hydrocarbon group optionally having one ormore halogen atoms, a C3-C7 cycloalkyl group optionally having one ormore halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group optionallyhaving one or more halogen atoms, a phenyl group optionally having oneor more substituents selected from Group D, or a 5 or 6 memberedaromatic heterocyclic group optionally having one or more substituentsselected from Group D; R¹⁴ represents a C1-C6 chain hydrocarbon groupoptionally having one or more halogen atoms, a C3-C7 cycloalkyl groupoptionally having one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3alkyl group optionally having one or more halogen atoms, or aphenylC1-C3 alkyl group {the phenyl moiety in the phenylC1-C3 alkylgroup may optionally have one or more substituents selected from GroupD}; R¹⁵ and R¹⁶ represent independently of each other, a C1-C6 alkylgroup optionally having one or more halogen atoms; n represents 0, 1, or2; p represents 0, 1, or 2; and R⁶ represents independently of eachother a C1-C6 alkyl group optionally having one or more halogen atoms, aOR¹⁸, a NR¹⁸R¹⁹, a cyano group, a nitro group, or a halogen atom, andwhen p is 2, a plurality of R⁶ may be identical or different; Group B: agroup consisting of a C1-C6 alkoxy group optionally having one or morehalogen atoms, a C3-C6 alkenyloxy group optionally having one or morehalogen atoms, a C3-C6 alkynyloxy group optionally having one or morehalogen atoms, a C1-C6 alkylsulfanyl group optionally having one or morehalogen atoms, a C1-C6 alkylsulfinyl group optionally having one or morehalogen atoms, a C1-C6 alkylsulfonyl group optionally having one or morehalogen atoms, a C3-C6 cycloalkyl group optionally having one or morehalogen atoms, a cyano group, a hydroxy group, and a halogen atom; GroupC: a group consisting of a C1-C6 chain hydrocarbon group optionallyhaving one or more halogen atoms, a C1-C6 alkoxy group optionally havingone or more halogen atoms, a C3-C6 alkenyloxy group optionally havingone or more halogen atoms, a C3-C6 alkynyloxy group optionally havingone or more halogen atoms, and a halogen atom; Group D: a groupconsisting of a C1-C6 chain hydrocarbon group optionally having one ormore halogen atoms, a hydroxy group, a C1-C6 alkoxy group optionallyhaving one or more halogen atoms, a C3-C6 alkenyloxy group optionallyhaving one or more halogen atoms, a C3-C6 alkynyloxy group optionallyhaving one or more halogen atoms, a sulfanyl group, a C1-C6alkylsulfanyl group optionally having one or more halogen atoms, a C1-C6alkylsulfinyl group optionally having one or more halogen atoms, a C1-C6alkylsulfonyl group optionally having one or more halogen atoms, anamino group, a NHR²¹, a NR²¹R²², a C(O)R²¹, a OC(O)R²¹, a C(O)OR²¹, acyano group, a nitro group, and a halogen atom {R²¹ and R²² representindependently of each other a C1-C6 alkyl group optionally having one ormore halogen atoms}; Group E: a group consisting of a C1-C6 chainhydrocarbon group optionally having one or more halogen atoms, a C1-C6alkoxy group optionally having one or more halogen atoms, a C3-C6alkenyloxy group optionally having one or more halogen atoms, a C3-C6alkynyloxy group optionally having one or more halogen atoms, a halogenatom, an oxo group, a hydroxy group, a cyano group, and a nitro group;Group F: a group consisting of a C1-C6 alkoxy group optionally havingone or more halogen atoms, an amino group, a NHR²¹, a NR²¹R²², a cyanogroup, a phenyl group optionally having one or more substituentsselected from Group D, a 5 or 6 membered aromatic heterocyclic groupoptionally having one or more substituents selected from Group D, aC3-C7 cycloalkyl group optionally having one or more halogen atoms, anda 3 to 7 membered nonaromatic heterocyclic group optionally having oneor more substituents selected from Group C.